


Two Plus Two Equals Three

by justanotherbusyfangirl



Category: Supernatural
Genre: All the Smut, Amnesia, Beard Kink, Blowjobs, Bondage, Canon-Typical Injury, Canon-Typical Violence, Caudaulism, Clothes Sharing, Cockwarming, Coitus Interruptus, Dom/sub, Double Penetration, Dry Humping, Grace Kink, Impala Sex, M/M, Masturbation, Omorashi, Panty Kink, Pegging, Polyamory, Praise Kink, Rimming, Road Head, Sex Toys, Shower Sex, Size Kink, Smut, Some Plot, Somnophilia, Sounding, Spanking, Teasing, Vaginal Fingering, Voyeurism, Wing Kink, accent kink, bed sharing, female!Sam, role play, switch!cas, switch!dean, switch!sam
Language: English
Status: Completed
Published: 2019-08-05
Updated: 2019-09-30
Packaged: 2020-08-09 18:24:09
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 25
Words: 25,712
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20122852
Author URL: https://archiveofourown.org/users/justanotherbusyfangirl/pseuds/justanotherbusyfangirl
Summary: Dean and Sam have always had this thing.  But then Dean starts feeling some things for Castiel, too, just before a hunt goes terribly, terribly wrong.  Can the three of them make it through the hunt without ruining their relationship, or will the hunt help create something even better than before?This fic covers bingo fills for @spnkinkbingo, @samwinchesterbingo, @deanandsambingo, @deanandcasbingo, @spnpolybingo, @heavenandhellbingo, and @badthingshappenbingo.  See each chapter’s notes for specific fills.





	1. Chapter 1

**Author's Note:**

> This chapter covers the Sex Toys square for SPN Kink Bingo, and the Sex Toys square for Sam Winchester Bingo.  
[Here's the toy in question](https://www.tantusinc.com/collections/dildos/products/echo-handle?variant=529312557)

It started not too long after Stanford. 

Sam kept his college experimenting a secret from Dean, unsure of how his brother would react to the fact that his baby bro sometimes liked it up the ass. Sam knew that John would have been ashamed, yelled at him for the wrongness of it all, and he figured Dean would be just the same.

Little did he know, it turned out.

They were heading for Bobby’s to get as much R&R as they could before another hunt came up. Sam had quickly ordered the package from a website that promised discretion, calling the post office in Sioux Falls to make sure they held it there and didn’t deliver it to Bobby’s house.

It was easy enough to pick up, since Bobby took a day for himself to deliver a book to another hunter and Dean absolutely did not want to do the grocery store run. Sam happily went shopping, with a pitstop at the post office on the way home.

He opened the box in the car and stuffed it in his backpack after admiring it for a moment, his stomach twisting with anticipation. He didn’t want to take the box inside and risk Dean asking what he’d gotten, better to carry it in his backpack, which Dean rarely looked inside of.

Sam thought he’d done pretty well, actually, with how casual he was when he went inside. He helped Dean unload groceries while his backpack stayed snug on his shoulders. Sam then ran it up to his room, grateful for the hundredth time that Bobby’s house was large enough that he and Dean didn’t have to share rooms when they stayed there.

Sam was a bit twitchy through dinner, feigning restlessness that he used as an excuse to take a shower and go to bed early.

Once he’d grabbed his backpack and a change of clothes, he shut the bathroom door behind him, carefully taking it out of his backpack.

It was purple and long, with a handle on the end for thrusting. There were ridges along it, sure to make Sam’s hole flutter with each in and out movement.

He washed it carefully in the sink as the shower ran behind him before he stripped his clothes off. He coated his fingers with lube, reaching behind to open himself up.

He took his time, the steam of the bathroom calming his body even as he got harder and harder from the stimulation. When he was open enough for the dildo, he slathered it with lube and notched it at his ass, finding the best grip on the handle.

Leaning over the sink, his feet planted wide, Sam slid the dildo inside of him. He bit his free fist to muffle his grunt of pleasure, wanting more already but also keeping himself under control.

It had been so long since he’d had anything inside of him, he wanted this to last.

Soon enough, Sam was fucking himself on the dildo, not touching his weeping cock that bobbed between his legs. He’d have to make sure he cleaned the bathroom floor, with how much precome was dripping from his swollen head.

Just as he was getting close –

The bathroom door opened.

“Dude, how long does it take to sh-“ Dean’s words stopped in his throat as he saw the picture in front of him: Sam leaning over the sink, fucking himself with a long purple dildo instead of taking the shower he’d claimed to need.

“Dean!” Sam squealed, a sound he’d forever deny. He tried to stand too fast, making the dildo uncomfortable inside of him. He turned slightly instead, covering his cock with a hand towel.

Dean shut the door, but instead of shutting the door and _leaving_, like Sam expected him to, he shut himself in the bathroom with Sam.

A few unreadable emotions crossed Dean’s face before it landed on one Sam recognized. Lust. “Damn, Sammy,” Dean said, his voice smooth as butter. “Why didn’t you tell me you needed a good fucking?” Dean stepped close to Sam, looking around to admire the purple handle that was sticking out of Sam’s ass, as the toy was still snug inside of him. “That’s a nice toy you’ve got there.”

Sam’s eyes were wide, but he was still horny and Dean was standing awfully close. And he wasn’t disgusted by Sam, in fact he seemed… interested?

“Dean?” Sam said quietly, a million questions hiding in the name.

Dean smiled, biting his lower lip for a moment to make it pink and perky. “Want some help?”

Sam’s eyes grew wider, if that’s possible, and he nodded before he realized what he was doing. Dean’s hands were gentle on Sam’s shoulders as he turned Sam back toward the sink, moving him into the same position that he’d been in before Dean surprised him. For a minute Sam wasn’t sure what Dean was doing, just standing there, but Dean was taking his time to admire the ass in front of him. 

“Damn, Sammy,” Dean repeated. “Where have you been hiding?” Dean’s hand found the grip on the dildo and he started to move the toy again, making Sam whimper. 

It didn’t take long for Dean to find the right angle so that the head of the dildo hit Sam’s prostate with every movement. Sam quickly came all over the floor, teeth marks sure to leave a bruise on his fist with how hard he was trying to keep quiet.

Dean pulled the dildo from his brother’s hole, catching his thumb against the rim to tease Sam just a bit. “Dean…” Sam groaned, his blush covering his entire back. Dean smiled and looked from the toy in one hand to his brother’s ass.

“What do you say we actually get in the shower and you try this thing out on me?” Dean asked, sounding a hell of a lot more confident than he felt.

Sam stood, turning to look at Dean in the eyes. Dean’s eyes couldn’t hide a thing from Sam, not after the years of admiration and devotion Sam had given him. He saw the nervousness in Dean’s eyes, but he also saw the arousal and lust.

“I say that sounds like a wonderful idea,” Sam replied, taking the dildo from his brother. “You need less clothes, though.”

Dean was hasty to strip, the two of them quickly figuring out just how tight the shower was for two grown men and a purple dildo.


	2. Chapter 2

**Notes for the Chapter:**

> This chapter covers the Dom!Sam square for the Sam Winchester Bingo, the Sub!Dean square for the SPN Kink Bingo, and the Spanking square for the Dean and Sam Bingo.

Sam hobbled into the motel room, Dean’s arm wrapped around his shoulder as Sam held him up. Dean’s shirts were drenched with blood in various places from the scratches he’d sustained fighting the werewolf.

Scratches he would have never gotten if he’d just let Sam take care of himself.

Sam had already yelled Dean’s ear off in the car, though, and was now tired of telling his brother to let him fight his own battles. Dean didn’t listen, he never did when it came to taking care of Sam.

Sam knew that, but he also had one more way to get the message into Dean’s thick skull…he just needed to patch Dean up first.

He kicked the door closed before angling Dean to the bed, letting him fall to his uninjured side while Sam grabbed their med kit. Dean’s face was scrunched in pain, although he would just call it discomfort, when Sam turned back toward him.

“Shirt,” Sam said sternly, “Off.”

Dean moaned before sitting up, careful hands taking his outer layer off before reaching for the hem of his t-shirt.

Sam watched as Dean moved slowly before reaching out to help. He was surprised when Dean let him take the shirt the rest of the way off, revealing the scratches to Sam’s eyes.

They really weren’t all that bad, Sam saw, just shallow and long, with deep bruises already forming beneath the surface. One set started at Dean’s right shoulder, crossed his pec and ended just above his belly button. Another set started on the left side of his stomach, wrapping around the side of his body and ending at his low back. That could have been much worse, if it were any deeper.

Dean had other bruises and bumps from the fight, but those scratches were the worst. He drenched a washcloth in rubbing alcohol and started cleaning Dean’s cuts, ignoring the hiss of air through Dean’s teeth as it stung.

Once the blood had been wiped away and the wounds cleaned, Sam could confirm that there was no serious damage, no muscle or internal organs injured. It was skin and subcutaneous tissue that the scratches had torn through, not much deeper.

With the length of the scratches, though, Sam had to wrap Dean’s entire torso to cover the wounds. As he was starting, Dean’s hand caught Sam’s.

“Let me just call Cas, he can heal –“

“No,” Sam said loudly, cutting Dean’s words off. Dean looked surprised. “Maybe later, but right now I’m patching you up and then we’re having a chat.”

Sam’s voice held power in it, a sense of authority that he usually didn’t use in their day-to-day lives. In fact, that tone of voice was one Sam only used with Dean in one situation…

Blood rushed southward as an automatic response to Sam’s dominance. Dean’s eyes widened and he nodded, shrinking in on himself just slightly.

Sam watched Dean’s reaction and seemed to be pleased with it, seeing as he continued to wrap Dean in gauze and bandages.

When he was finished, they were both completely silent as Sam put the med kit away, mentally noting that they’d need to buy more supplies the next time they were in a convenience store. He turned to put the kit away and took a deep breath, finding his headspace.

When he was there, he turned to Dean.

The injured man was sitting with his hands on his knees, eyes lowered submissively. Sam smiled.

“What’s your safeword?” Sam asked.

If Dean wasn’t in the mood, he would tell Sam now.

“Poughkeepsie,” Dean answered, letting Sam know that he had permission to continue.

The corner of Sam’s mouth quirked up and he started to roll his sleeves up. “Strip.”

The simple command was followed without hesitation. Dean tried his best not to grimace at the movement of his injuries, too invested in taking off his boots, socks, pants, and boxers. Soon he was standing by the bed, his semi-hard cock pointed toward Sam like it was asking to be held.

Sam walked over to Dean, his fingertips grazing the bandages across Dean’s chest. “Do you not think I can take care of myself, Dean?” Sam asked softly, his voice still holding the air of authority even at its quiet level.

Dean swallowed.

“Answer me,” Sam ordered, louder now.

“Yes, sir,” Dean said quickly. “You can take care of yourself, sir.”

Sam nodded. “So why do you insist on diving in front of me, when I’m perfectly capable of fighting for myself?”

Dean’s eyes raised to meet Sam’s, but quickly looked down again. “Sorry, sir,” he answered, not answering the question but at least showing some admittance of the situation.

“Hmm,” Sam responded, sitting down on the edge of the bed. His feet were flat on the floor, making his lap steady and strong. “With no valid explanation, I do believe a punishment is necessary.”

Dean whined somewhere deep in his throat, but was smart enough to not let it fully form. He nodded, letting Sam lower his body across Sam’s lap – carefully to not press on any of the newly bandaged cuts – so that his bare ass was sticking up, plump for Sam’s hand to fall onto.

Sam felt the globe of each cheek, squeezing to get blood flowing to the area. “How many do you think it will take, Dean, to teach you this lesson?”

Dean was quiet for a moment before answering. “Forty, sir.”

Sam’s eyebrows raised at the high number. “Forty, huh?” Sam tapped Dean’s right cheek in an easy pat, smiling when Dean’s body jumped in response. “That’s awfully good of you, Dean. Let’s do twenty and decide from there, how about that?”

Dean nodded, his head falling down to hang free. Sam rubbed Dean’s ass a bit more before bringing a hand down firmly. He knew that his spankings weren’t forgiving, and the fact that Dean had offered for forty was impressive. Dean’s body jerked at the smack of palm on skin as he quietly counted. “One.”

Sam alternated cheeks for a while, before spreading his fingers to land on Dean’s entire ass. Soon Dean’s skin was a nice pink color, the blood pooling under the surface like a sunburn.

At twenty, he stopped.

“What do you think, Dean, have you learned your lesson?” Sam asked, hand soothing the smarting skin. Dean breathed deeply and Sam could feel Dean’s erection poking against his leg.

“Maybe, sir,” Dean finally replied. Sam chuckled. 

“Maybe earns ten more, then,” Sam stated. These ten were quick, but no less painful. When he was done, Sam turned Dean to cradle him in his lap, careful to not rub Dean’s tender flesh against Sam’s rough jeans.

“Such a good boy for me, Dean,” Sam praised, kissing Dean’s forehead before reaching his hand to grasp Dean’s hard and leaking cock. It only took a few, practiced tugs before Dean was spilling all over himself, crying out in relief as he came.


	3. Chapter 3

**Notes for the Chapter:**

> This chapter covers the Masturbation square for Dean and Sam Bingo, and the Somnophilia square for SPN Kink Bingo. (the somno is consensual)

Dean barely needed any coaxing to go to sleep once they’d finished their scene. Sam held Dean in his arms for a while, soothing his brother in a way only he could, before laying him out on the bed and cleaning them both off.

Dean curled up on his side, humming his pleasure as Sam rubbed lotion over his red ass. The massage soothed him until he was sleeping soundly, a faint smile on his face as he dreamed.

Sam watched Dean sleep for a while, running his fingers up and down Dean’s body softly. The bandages hadn’t dislodged during their scene, which was good, and Dean’s ass was already returning to its normal color. Sam had gotten good at knowing just how much punishment Dean could handle before causing serious damage, not wanting an unexpected hunt to come up where Dean would have bruises in various places.

Finally Sam stood, his own erection reminding him that while he’d gotten Dean off, Sam didn’t take care of himself.

He sighed, looking back at Dean in the bed. He looked so handsome, laying there…

Sam’s hands were stripping himself of his clothes before he realized it, and soon he was standing over Dean, jacking himself off. 

He gazed at the curve of Dean’s jaw, thinking about how pretty Dean looked with Sam’s cock in his mouth. He tightened his hand around the head, imagining Dean’s throat tightening around it as he’d swallow Sam as far as he could.

Sam’s eyes trailed across Dean’s covered chest, stomach churning for a second at the thought of Dean’s injury, before eyeing Dean’s cock. It was spent and sleeping, just like Dean, but it was still delicious. Sam tugged at his cock, thinking about how awesome it felt when they just rubbed against one another, cocks aligned perfectly.

Sam bit his lip, desperate for more.

He looked again at Dean’s ass, now just a pretty pink instead of the bright red after his spankings. It was round and plump, as always, with a light smattering of hair. He reached out before he could stop himself, grabbing at one cheek so that he could pull it slightly to reveal Dean’s tight hole.

Dean shifted in his sleep, sighing as he rolled a bit further onto his stomach. Sam wondered for a minute if Dean was awake and inviting Sam…

A snore told Sam otherwise.

Sam’s cock was hard as a rock as he stroked it, his thumb sliding between Dean’s cheeks to press at his hole. It fluttered a bit, but allowed a bit of intrusion.

Sam couldn’t take it anymore, he turned away and reached for his duffel. Lube was found quickly and soon Sam was drizzling it across Dean’s hole, pressing a thick finger inside.

“Dean…” Sam groaned, entranced at the sight of his finger disappearing. Dean rolled further onto his stomach, body relaxed and pliant. Either he was dead to the world or just pretending, but either way Sam knew Dean wouldn’t object.

It didn’t take long to work up to three fingers inside of his brother; it hadn’t been too many nights since their last session of good, old-fashioned fucking. Sam slipped his fingers from Dean’s body and lubed himself up before climbing on top of his brother. He got a knee on either side of Dean to straddle his legs and slid his cock between Dean’s cheeks a few times before notching himself at the entrance.

As was habit, Sam leaned down to nibble on Dean’s ear as he pushed inside, his breaths heavy against Dean’s face. Dean was hot and pliant, making Sam’s cock pulse when he seated himself inside.

“Fuck, De-“ Sam moaned. His body was draped over Dean’s prone form, hot with stimulation. He gave himself a moment to savor the feeling before pushing up to his knees. He held Dean’s hips with his huge hands and started to pull out, watching as Dean’s body gave way to Sam’s cock.

The sight was to die for. 

Sam wasn’t in any hurry, so he started a lazy roll of his hips, eyes watching as inch after inch of his cock slipped inside and then was revealed again. He couldn’t look away, he was entranced with the push and pull of their bodies together.

He wasn’t sure how long he’d been enjoying himself before Dean’s ass tightened around him, a small noise of surprise sounding against the pillow. Sam almost stopped, but he found he didn’t need to.

“Come on, Sammy,” Dean’s sleepy voice said. “Go to town already.”

Sam grinned, shifting his position so that he could raise Dean’s hips slightly. Dean still didn’t bother taking control of his body, but let Sam position him just how he needed.

“Hold on,” Sam muttered, watching Dean’s hand clench at the pillow before he began a pounding pace, his hips slapping against Dean’s ass with each thrust.

It wasn’t long until he was coming, his body more than ready after the long and slow build-up. Dean took it in stride, squeezing around Sam’s cock as he finished.

Sam pulled out, rolling to the side to place a kiss on Dean’s lips. He was surprised to see a mess on the blanket and Dean’s stomach, indicating that his brother had come again.

Dean snorted. “You play me easy, awake or asleep.” Sam grinned. “But you get to clean me up, ya freak.”

Sam leaned over to kiss Dean again before grabbing another washcloth. He returned to the bed, stripped it of its soiled blanket, and washed Dean off before tucking them both in, sleep coming quickly and easily wrapped up together.


	4. Chapter 4

**Notes for the Chapter:**

> This chapter covers the Accent Kink square for SPN Kink Bingo.

Dean prayed to Castiel the following morning, knowing that it would be better for Castiel to heal the wounds before they used up all their medical supplies and he ended up with ridiculous, jagged scars.

With the morning and breakfast came Sam finding a new case, so the three of them strategized. There was some strange business happening in southwest Kansas, but Donna had some books that she needed to return to them as well. They decided to split up – Sam heading for the case, by way of the bunker to stock up on some supplies, while Dean and Castiel would stop at Donna’s quickly on their own way.

The open road was easily one of Dean’s favorite places to be, even if Sam wasn’t the one in the seat next to him. They’d had plenty of alone time (specifically in the last 24 hours), so Dean was happy just having Castiel’s company.

Plus, he was enjoying teaching Castiel about human things.

Dean had been slipping random hunting tips into conversation with Castiel for what seemed like forever now, and Castiel was only just now starting to apply some of them to their hunts. He needed a lot of practice on some things, like interrogation, but others had just worked out pretty naturally for the angel.

Which is why, when they stopped for gas and snacks on the way back from Donna’s, Dean was suddenly surprised by his friend.

Castiel had grabbed a few things to snack on and was at the counter talking with the girl working. As Dean approached, he heard a voice that sounded very different from Castiel’s natural voice.

“Howdy, sweetheart,” Castiel greeted, an unfamiliar drawl in his voice. “How ya doin’ this fine day?”

Dean watched as the girl blushed, finding Castiel endearing at least. She said something back, but Dean didn’t pay too much attention. He was too busy trying to figure out what Castiel was doing.

Their conversation continued, Castiel continuing with this low drawl in his voice, a fairly good southern accent if Dean would admit it. Castiel’s voice was entrancing, the growly nature of the r’s rolling around in Dean’s head, the diphthongs merged together so smoothly that they sounded like a single sound.

Suddenly Dean was feeling very hot and he needed to get out of the convenience store. He dumped his items in front of Castiel, muttering a, “You’re paying,” before heading outside and around to the restroom.

He got inside and locked the door, turning to the sink and getting the cool water going. He splashed his face a couple times before glancing down.

Dean was rock hard, just from hearing Castiel’s voice in there.

That sort of thing hadn’t ever happened to him before. ‘Cause sure, he loved old western movies with their drawling, handsome stars, but that was when he was in his room alone. This was public, in person…getting a hard-on from his _friend’s_ voice.

He didn’t want to think about it too much right now, because he was about to have to sit in the car for another six or more hours and refused to be uncomfortable with an unattended erection. Dean quickly undid his pants, pulling his cock out of the slit of his boxers. He jacked off over the sink, closing his eyes and picturing Sam’s cock.

But suddenly, it wasn’t Sam’s cock he was picturing, but Castiel’s cock – which in his imagination was perfect. He heard Castiel’s drawling voice in his ear, but soon the voice wasn’t accented anymore, it was just Castiel’s normal voice. _“Hello, Dean,”_ Castiel’s voice said in Dean’s head, just before Dean spilled into the sink.

He didn’t notice the moaned, “Cas,” that escaped his mouth as he came. He was quick to run the water some more to clean his hand and the ceramic bowl before making himself presentable again.

Dean especially didn’t notice that Castiel was awkwardly quiet in the car, having overheard a bit of Dean’s private time and a sensually moaned name.


	5. Chapter 5

**Notes for the Chapter:**

> This chapter covers the Road Head square for SPN Kink Bingo.

The first hour or so of the car ride was silent, both men lost in their own thoughts. Dean was still somewhat confused at his body’s reaction to Castiel’s accent, while Castiel was piecing together Dean’s actions from the check-out of the store to the moan in the bathroom.

Castiel found himself glancing at Dean multiple times, thinking of the way he’d moaned Castiel’s name in the bathroom. He was still learning the intricacies of human interactions and habits, but he was fairly certain that the moan in question had been a good one.

Castiel’s body had a reaction to it, at least.

Finally Castiel spoke.

“Dean, are you okay? You seemed a bit off at the convenient store.”

Dean started at the unexpected question, glancing at Castiel across the car. He looked back to the road and shifted in his seat. Castiel saw out of the corner of his eye as Dean adjusted the front of his pants, smiling slightly as his suspicions were confirmed.

“Fine, Cas,” Dean said gruffly. Castiel turned toward Dean, leaning against the door a bit. Dean looked over at him again, but quickly looked away as a stain of pink crept up his neck and cheeks.

“You still seem a bit…” Castiel searched for a word that wouldn’t be offensive or terribly blunt, “anxious.”

“Pfft,” Dean replied, unconvincingly. “I’m not anxious.”

Dean shook his own head at his quick words, knowing that he wasn’t going to trick anyone, even Castiel, who was sometimes slow on picking up nuances in speaking. One more glance toward Castiel proved to him that the angel wasn’t buying what Dean was selling.

In fact, this glance to Castiel caught the angel looking down at Dean’s crotch.

Dean shifted again, willing his growing erection to just _stop it_. How he was even getting it back up so quickly was beyond him.

The silence was heavy in the car, stifling. Dean could feel Castiel’s eyes on him, like he was running a finger down Dean’s body. Every second that passed had Dean getting harder, for reasons he couldn’t seem to compute.

He thought of Sam, but shook his head. Yes, he and Sam had been together for what seemed like forever, but they had an understanding. When they were apart, or needed something a little different…

But this was Castiel. Surely it was different, yes?

In a sudden and sure movement, Castiel pushed away from the door and across the front seat until he was crowding Dean’s space. Dean froze, eyes on the road, not sure if he was silently willing Castiel to continue or asking him to stop.

His body didn’t want Castiel to stop, though.

Castiel’s breath warmed Dean’s ear as he whispered, “I heard you in the restroom, Dean.” Dean shivered. “I heard you say my name.”

Dean blinked, eyes trying to keep focused on the road. His hands gripped tighter on the steering wheel. When he didn’t answer, Castiel continued.

“Tell me why you said my name, Dean.” Dean could have sworn that for a gentle second, Castiel’s teeth nipped his earlobe. “Tell me.”

Dean licked his lips. Staying completely still, he answered. “I, uh,” Dean stammered, swallowing before trying again. “Your accent, uh…got to me.”

Castiel laughed, a low chuckle that sent goosebumps down Dean’s spine. His cock was now rock hard, straining against the zipper of his jeans even though he’d just come over an hour before. He shifted, trying to ease the tightness.

His movement only captured the attention of Castiel, who leaned back slightly to look down at Dean’s crotch. “You seem uncomfortable, Dean,” Castiel commented, sounding a bit more like himself than the sultry voice that had been in his ear a moment before.

It didn’t sound any less sexy, especially when Castiel’s hand landed on Dean’s knee and squeezed.

“Tell me to stop, Dean,” Castiel said as his hand moved up Dean’s leg. Dean’s mind whirred, but he knew without a doubt that telling Castiel to stop was the last thing he wanted to do. After the thing at the gas station and the way Castiel was acting now…he wanted Castiel more than he ever had before.

Dean shifted his hips forward, encouraging the journey of Castiel’s hand up his leg and toward his crotch. Castiel received the message loud and clear, moving to cup Dean through his jeans.

The pressure of Castiel’s hand made Dean groan loudly, angling his hips upward even more. 

Castiel smiled.

Quickly, and with surprising deftness, Castiel undid Dean’s jeans and pulled his cock out through the slit in his boxers, exposing the hardness to the air of the car and Castiel’s view. Castiel hummed, licking his lips at the sight.

“You have no idea how beautiful you are, Dean,” Castiel commented as he started to jack Dean’s cock. Dean’s hands shifted on the wheel, knowing that he didn’t want Castiel to stop touching him, but also knowing that he needed to keep Baby safely on the road.

“Cas-“ Dean said, an encouragement or order, he couldn’t tell.

Either way it was received, Castiel shifted his position yet again so that he was laying flat on the bucket seat, sliding Dean’s cock into his mouth. The sudden heat and wetness around Dean’s head had him huffing in surprise, a tiny jerk of the wheel all he allowed himself.

Dean concentrated on the pressure of his foot on the gas pedal and keeping the wheel straight as Castiel bobbed on his cock. He was sloppy but enthusiastic, and Dean knew he wasn’t going to last.

“Cas, Cas…” Dean chanted, wanting to encourage his friend.

Castiel sucked, licked, and bobbed until Dean was coming down his throat with a gasp. Castiel worked Dean’s cock until it started to grow limp, then sat up and tucked Dean back into his pants.

Castiel moved back to his side of the car, taking a few deep breaths to calm his thundering heart. He was exhilarated, but also terrified of the repercussions, from what he just did. He hoped Dean wouldn’t hate him.

A few minutes of heavy silence later, Dean’s hand left the steering wheel to reach for Castiel. His hand rested easily on Castiel’s knee, squeezing a reassurance.

When Castiel glanced over at Dean, it was to see the hunter smiling softly.

That’s when Castiel knew everything would be okay.


	6. Chapter 6

**Notes for the Chapter:**

> This chapter covers the Rimming square for SPN Kink Bingo, and the Teasing and Overstimulation square for Dean and Sam Bingo.

The rest of the car ride passed quickly, but neither Castiel nor Dean spoke. Dean seemed happy with the silence, save for the cassette tapes playing in the background, and Castiel knew the hunter well enough to give him time.

As night fell and they got closer to the bunker, Dean’s hand left Castiel’s leg. Castiel wasn’t sure if it was so that Dean would have both hands to navigate Baby on the dusty roads, or if he was thinking of other things, but he pushed away any worries.

Dean, however, was starting to panic.

Sam was in the bunker. Sam, his brother, his rock, his lover.

And here was Dean, driving up to the bunker with his best friend who just gave him a (albeit, awesome) blowjob.

Dean pulled into the garage, turning Baby off before looking over at Castiel. Castiel was watching him for guidance, so Dean quirked the corner of his mouth up into a half-smile.

“We should probably get these books in to Sam,” Dean said lamely, opening his door to get out before Castiel could answer. They silently unpacked the car and headed inside, finding Sam in the library. It was late and Dean was sure that Sam had been sitting there reading ever since he’d gotten to the bunker hours before.

“Hey, let’s get a fresh start in the morning,” Dean said, clapping Sam’s shoulders and squeezing affectionately.

Sam started, obviously not having heard Dean and Castiel arrive. He chuckled. “Yeah, uh… yeah.”

Sam’s lame agreement made Dean laugh, but he headed to the hallway. He looked back at Castiel for a minute, feeling awkward.

“Night, Cas,” Dean finally said, after Sam marked his place in the books laid on the table and stood. Dean nodded at Castiel before turning and heading down the hall, hoping to figure things out in his head.

He was happy to hear Castiel return his, “Goodnight,” to both his retreating back and Sam, who said something in return. Soon Dean heard his brother’s footsteps following him down the hallway and to the showers, where Dean stripped and started the water.

He started going through the motions, his mind whirring a thousand miles a minute. Thoughts of him and Sam, the years they’d spent together, mixed with memories of the car ride with Castiel. He found himself thinking of the times that Sam had sucked him off, comparing it to the feeling of Castiel from earlier.

Dean dipped his head underneath the spray, closing his eyes to the stream. Maybe the water would wash not only his body, but what was in his mind as well.

Sam joined him, pushing Dean out of the water gently so that he could rinse himself. They danced around one another, movements fluid and easy from practice. Dean thought Sam started to speak a few times, but words never came.

As they were drying off, Dean bumped Sam’s shoulder. “I’ll meet you in your room.”

Sam heard the underlying meaning that Dean was trying to say. _I need you_.

Dean headed for Sam’s room, dropping his towel by the door and getting onto the bed. His cock was half-hard, but he ignored it.

For whatever fucked up reasoning in his mind, Dean didn’t feel like he deserved to come.

Dean climbed onto Sam’s bed, kneeling in the center. He breathed in and out, slowly to steady his mind, before lowering his head to the mattress. He brought his arms to rest above his head, arching his back obscenely until his ass was sticking straight up into the air, knees as far apart as he could make them before it was uncomfortable.

He felt his cock hang heavy, the submissive position sending more blood southward.

The door opened and shut, the lock clicking loudly in the room. Dean listened as Sam moved about, probably ridding himself of his towel and taking note of Dean’s position.

Finally a strong hand fell on Dean’s lower back.

“Should I allow you to come tonight, Dean?” Sam’s low voice questioned. Dean sighed, grateful that Sam could practically read his mind. At the same time, Dean was grateful that Sam couldn’t _actually_ read his mind, but just his body language.

“Not tonight,” Dean answered. Sam moved away.

His voice sounded from the foot of the bed this time. “What’s your safeword?”

Dean turned his head away from the bedspread for a moment so Sam could hear him clearly. “Poughkeepsie.”

“Good,” was all Sam replied. He climbed onto the bed between Dean’s feet, his hands falling onto Dean’s ass. It had recovered from the spankings, but Sam massaged the flesh anyways. He loved Dean’s ass and everything about it. It was perky and plump, while usually hiding the most secretive place of Dean’s body.

Now, though, Dean’s anus was available to the room, with the submissive pose Dean had gifted Sam. Sam smiled before leaning forward, running his tongue from the base of Dean’s balls, up his perineum, and over the dark pucker of skin.

Dean twitched but kept silent, burying his face further into the bed.

Sam got to work, laving Dean’s crack with kisses and licks until it was covered in spit. His tongue flicked across the hole, loving the way Dean’s body clenched in response to every touch. Dean couldn’t keep all of his noises to himself, even though he was trying. Sam took that as a challenge, needing to hear Dean lose control.

Sam sucked at Dean’s hole before pointing his tongue and pushing inside, tasting the musk that was Dean. He brought a thumb up to help pull at Dean’s hole so that his tongue and the tip of his thumb could stretch Dean wider, teasing the sensitive skin until finally Dean was whimpering.

“You like that, Dean?” Sam mumbled, pulling back slightly to spit onto Dean’s ass before diving back in. In the split second that Sam took his face away from Dean’s ass, he saw the dribble of precome hanging between Dean’s cockhead and the comforter. 

Sam sucked at Dean’s hole again before pushing inside with his tongue even further. Dean moaned, so Sam started to fuck him with his tongue. His back was starting to ache, but he wasn’t going to stop until he was satisfied.

Dean might not want to come tonight, but Sam was going to make sure he was pretty damn close.

Sam listened as Dean’s breaths got more and more frantic, knowing exactly what to listen for when it came to his brother and orgasms. His mouth worked harder and faster at Dean’s ass, pulling out all the stops to tease Dean.

When Sam finally heard the high whine bubbling out of Dean’s throat, one hand moved to grab the base of Dean’s cock – hard. He squeezed just right to make sure that Dean wouldn’t come – his fingers forming an almost-painful vice to keep Dean grounded.

His mouth kept going, though.

Sam’s tongue kept fucking into Dean, pulling at the sensitive flesh around Dean’s hole. Every flick of Sam’s tongue was sending zings of pleasure up Dean’s spine, he knew. Soon Dean would be begging him to stop…

Another whine from Dean made Sam realize that Dean might not ask him to stop. Why would Dean let him keep going, if he knew it would push him too far?

Sam slowly pulled his tongue from Dean, flattening it to stimulate the entire area around Dean’s hole a few times. He squeezed Dean’s cock one last time before letting go, moving away from Dean completely.

Sam watched carefully as Dean’s breaths slowed, his body relaxing. His cock was still full and heavy, but Dean didn’t move to relieve any pressure. When Sam was satisfied that Dean had calmed, he moved up the bed to rub his hand along Dean’s spine in a soothing gesture. 

“I think that’s enough, Dean,” Sam said softly. Dean lifted his face from the bed, creases from the comforter crossing his cheeks. He nodded.

“Thank you, Sam.”

Sam smiled, watching as Dean moved to tug at the covers. He chuckled, getting up so that he could pull the covers back and tuck them both inside.

Dean snuggled his face into Sam’s chest, exhaling deeply. Before Sam could say a word, Dean was sound asleep.

Sam would have to get Dean to open up tomorrow, then.


	7. Chapter 7

**Notes for the Chapter:**

> This chapter covers the Sounding square for SPN Kink Bingo and the Aftercare square for Dean and Sam Bingo.

When Dean woke the next morning, Sam told him that Castiel had left just after dawn for something. As horrible as it made Dean feel, he was actually relieved that he wouldn’t have to be around Castiel for a while.

He grudgingly sat down after breakfast to help Sam with research, the two of them following a trail of murders across the middle-US. Dean was more huffy than normal, so much so that Sam insisted that they take a break before lunch.

Sam stood before Dean, eyes narrowing at his brother.

“Bedroom, now,” Sam ordered. He watched as Dean considered fighting it before he nodded minutely and headed for the hallway, his posture changing from angry big brother to sub with every step.

Inside the room Dean stopped, waiting for instructions. Sam smiled.

“Clothes off, please, and on the bed.”

Dean went into motion as Sam moved to his dresser, opening the drawer where they kept their toys. His eyes considered a few options before settling on a pouch, which he took out and unrolled on top of the dresser.

Sam took his time cleaning the toys; even though he always cleaned them before putting them away he wanted to make sure they were cleaned again. He didn’t turn to check on Dean, knowing that his brother would be waiting, patiently or impatiently, for Sam.

Finally Sam was satisfied and turned around, cool metal in hand. Dean was laying on his back, head on the pillows. His eyes widened minutely upon seeing what was in Sam’s hand, but then Sam saw the telltale dilation of Dean’s pupils and his semi-hard erection twitched on his stomach.

Sam knew his brother well enough to know what kinds of things would get him in a better mood, that’s for sure.

“What’s your safeword?” Sam asked, never one to push Dean past his boundaries, even when Sam knew he was well inside of Dean’s limits.

“Poughkeepsie,” Dean sighed breathlessly.

In the time from when Sam turned around to Dean confirming his safeword, he had become fully hard. Sam went over to the bed, grabbing a bottle of lube on his way. He laid a fresh cloth next to Dean’s hip and the clean metal rod on top of it, uncapping the lube.

“You are tense, Dean,” Sam said quietly. He spurted lube onto his hand and stroked Dean’s cock, wanting to make sure Dean was hard enough to not get injured. “It’s time for you to relax a little.

Dean hummed, doing his best to keep his hips flat on the bed and not thrust up into Sam’s hand. He knew Sam’s rules: Dean would do what Sam said and _only_ what Sam said, or he would get punished. (Of course, sometimes Dean broke Sam’s rules on purpose, but he didn’t want that type of scene today.)

Sam worked Dean’s cock until he was satisfied. He let the shaft stand on its own as he reached for the sound, getting more lube to coat the rod.

With the sound in one hand and Dean’s cock in the other, Sam lined everything up perfectly. His eyes went from his hands to Dean’s face, seeing his brother watching everything with rapt attention.

“Relax, Dean.”

Dean met Sam’s eyes before nodding, letting his head fall back on the pillow. He took a deep breath in and let it out, his entire body expelling the remaining tenseness. Sam watched and listened for Dean’s next deep breath, using Dean’s exhale as the right timing to start working the sound into Dean’s urethra.

With each of Dean’s exhales, Sam worked the sound further into his body until it reached its furthest point. Sam let go of it for a moment, watching as Dean’s body reacted naturally to the intrusion.

Sam moved slowly, leaving the sound where it was and leaning forward to kiss Dean’s chest. His hair tickled Dean’s bare skin, but Sam felt Dean forcing himself to stay relaxed.

Sam peppered soft kisses across Dean’s pecs before giving his full attention to one of Dean’s nipples, worshipping it with his tongue and the occasional love bite.

Dean seized with each scrape of teeth, his hands clenching the bed on either side. Sam worked the nipple until he was satisfied and moved to the other.

This time, not only did he give Dean’s nipple attention, but his hand carefully found the end of the sound and began to pump it in and out of Dean’s penis. 

The combination of pleasure almost stripped Dean’s control from him. Sam listened and felt as Dean’s breath quickened, his body responding to the stimuli as he got more and more aroused. Sam smoothly moved from Dean’s nipple to kiss a trail down his chest until he was sucking a mark onto Dean’s hipbone, one eye watching his hand work Dean’s cock and the sound.

As Dean’s whimpers became more and more desperate, Sam sat back and brought his free hand to Dean’s cock, gently pumping it in rhythm with the movement of the sound. Dean’s eyes shot open and a shout left his mouth, a beautiful noise that Sam wanted to hear again and again.

“You didn’t come last night, Dean,” Sam said, his voice calm and smooth even in the heat of the moment. “I think you deserve to come now, don’t you?”

Dean whined instead of answering, which Sam might normally berate him for but he let it pass now. With a swift and sure movement, he slipped the sound from Dean’s cock and pumped his hand in time, making Dean come suddenly at the change of stimulation.

Dean’s spunk coated his stomach and hips, a creamy white mess. His eyes closed as Sam worked him through the aftershocks, snuggling into the bed as much as he could.

Sam smiled as he watched Dean relax, looking happier than he had all morning. At least Sam could help Dean relax.

Sam moved from the bed, hearing a small whimper as his body heat left Dean’s. “Shh,” Sam cooed, “I’ll be right back, I promise.”

He quickly went to the bathroom, putting the sound on the sink for him to clean and wetting a warm washcloth. He returned to Dean’s side, cleaning up the mess on Dean’s stomach before grabbing a blanket to pull around them both.

Dean’s body curled up against Sam’s, his legs crossing Sam’s lap. Sam let Dean nuzzle into his shoulder and he rubbed nonsense patterns on Dean’s back, kissing his hair every few moments.

It was these moments that Sam liked the most, after he took charge in the bedroom. Sure, being in charge of Dean – and Dean’s orgasms – was fun, but being able to take care of Dean afterward was even more rewarding.

Sam wouldn’t give this up for the world.


	8. Chapter 8

**Notes for the Chapter:**

> This chapter covers the Amnesia square for Heaven & Hell Bingo, the Vertigo square for Bad Things Happen Bingo, and the Free Space for Kink Bingo. This chapter is no smut, all plot! Imagine that!

Dean seemed better after lunch and the research moved along. By late afternoon they pinpointed the general location of what was probably a witch, and the rest of the evening was spent restocking Baby and getting rest so that they could leave at dawn.

Dean and Sam spent the night in their separate rooms, but neither of them felt strange about it. They shared a few kisses before parting in the hallway, knowing that they’d both be more rested if they slept alone. Dean wondered briefly what Castiel was up to, but before he got too deep in thought he’d fallen asleep.

Baby’s tires hit the pavement first thing the next morning and the brothers headed for western Illinois, wanting to get there as soon as they could to stop any more deaths.

Early afternoon had them dropping their stuff of at a motel and getting back in the car to drive around town. If Dean hadn’t known any better, he might have thought the whole situation was a trap with how easy it was to find the witch’s temporary digs in the town. Every stereotypical witch-y thing was pointing at one building: a little structure set far back from the road, far enough away from the buildings nearby that no one would spy or overhear anything. There were a few hastily painted symbols on the doors, ones that Sam was pretty sure were meant to ward from intruders.

The boys were quick to gear up, moving silently across the grounds until they were at the door. Sam eyed the symbol, making a face.

“I can’t remember if there will be a warning if we break the sigil, or if it will just be disarmed.”

Dean rolled his eyes, knowing that Sam was itching to check the books.

“We don’t have time to check,” Dean said. “Let’s just scratch it out and go in, if the witch gets a warning, we just need to be extra ready.”

Sam huffed, eyeing the symbol once more before whipping out his knife. He met Dean’s eyes, making sure they were ready to head inside. Dean nodded, so Sam scratched the paint on the door to break the symbol a second before Dean’s boot kicked the door in, gun at the ready.

They went inside, scoping the main room before seeing three doors. Sam went left as Dean went right, checking the two closest doors first. Their eyes met to confirm empty rooms before both of them headed for the third door.

The smell of some sort of smoke let them know that they were heading in the right direction, so Sam reached for the doorknob to let Dean count him down for an entrance.

In sync they burst through the door, finding a middle-aged woman in jeans and a black tank top waiting for them.

“Shouldn’t have broken the sigil!” she yelled, throwing her hands out toward the brothers. They were forced backward, flying through the air to hit the wall on either side of the door. The last thing they heard was the witch’s laughter as she ran from the room before everything went dark.

* * *

Sam’s head was pounding, but as soon as he realized that he was on the floor he moved to get up. That wasn’t a good idea, he realized quickly, because the room spun around him and he couldn’t seem to get his feet underneath him.

He shook his head, hoping to clear the cobwebs (it only made his balance worse, really) before getting onto all fours and heaving himself up to his feet.

Sam looked around the room, assessing the situation quickly. He didn’t know how much time had passed since he’d been knocked out. The witch was nowhere to be found, her things strewn about but now abandoned. He didn’t hear anything outside, so he assumed she’d run off, for now.

Dean was laying on the floor across the room, so Sam went to him. As he walked, he had a hard time balancing his weight and tripped a bit over something... He looked down to see what the issue was and frowned. His jeans were bunched up around his feet, and when he looked at his hands they seemed slimmer than normal.

“What the –“ Sam stopped his words in shock. His voice wasn’t its usual baritone timbre, instead much higher pitch. The room spun again, this time not because of a head injury.

Sam patted his hands along his body, confirming his suspicion. He was no longer in his own body – or his body had been changed drastically.

Sam was a woman.

“You’ve got to be kidding me,” Sam huffed, right as Dean groaned and rolled over. His hand went to his head, letting Sam know that Dean was probably just as dizzy as Sam had been when he woke up.

At least Dean was in his normal body.

“Whazza…” Dean said, voice confused and words slightly slurred. He stayed seated, not reaching for his gun. He looked around the room with squinted eyes until they landed on Sam.

Dean grinned.

“Heya, sweetheart,” Dean said, donning his normal, cocky attitude. “Who are you? And where are we?”

Sam sighed. “It’s me, Dean. Sam.” Sam looked back to the table that held some of the witch’s things. “That witch got us with something, knocked us out. I woke up like this.” Sam held his arms out as he looked back to Dean, who was now standing up.

“Sam, you said?” Dean asked, sauntering toward Sam with his trademark swagger. “That’s a pretty name, for a pretty girl.”

Sam rolled his eyes, ignoring his brother’s flirtations. “Are you gonna pick up your gun, Dean? She could come back any minute.”

Dean frowned, looking back to the floor where he’d been laying. “Gun? Why do I have a gun?” He looked back at Sam, who was holding his own pistol in his too-small hand. “Why do you have a gun? What the hell is going on?”

It was only then when Sam realized that there was actually something wrong. “Dean, what do you mean?”

Dean took a few steps backward. “Look, Sam, you’re awfully pretty. But I don’t know this Dean, and I don’t think I like guns very much.”

“You don’t…” Sam started, but he stopped himself. He stowed his gun in the back of his pants, which were a little baggy on his new body but luckily still kept the gun in place. “You don’t know who you are?”

Dean shook his head, looking around the room. “And where the hell are we anyway? It’s filthy in here. If I brought you here, which I’m sure I did,” Dean waggled his eyebrows suggestively at Sam, “I shoulda found a nicer place for us.”

Sam groaned, digging into his pocket. He found his cell phone, unlocking it manually and pulling up Castiel’s phone number. While the phone rang, Sam grabbed Dean’s gun from the floor. 

“Sam?” Castiel answered.

“Hey Cas, it’s Sam. We ran into a bit of a problem, can you come help?”

The line was silent for a moment.

“Does that problem include you having a more feminine voice than normal?” Castiel replied.

Sam laughed, although there was no humor in it. Dean had started to wander around the room, looking at the witch’s trinkets with open curiosity.

“Yeah, that and the fact that Dean doesn’t remember who he is.”

There was movement on the other end of the phone. “I’ll be there as soon as I can, Sam,” Castiel said before hanging up. Sam stowed his phone and went over to Dean, grabbing his arm.

“Come on, Romeo, let’s get out of here and to somewhere safe,” Sam said, as confidently as he could. Dean grinned at him.

“I’ll go anywhere with you, sweetheart.”


	9. Chapter 9

**Notes for the Chapter:**

> This chapter covers the Amnesia square for SPN Kink Bingo and the Dry Humping square for the Dean and Cas Bingo.

They headed to the Impala, where Dean promptly gushed over how pretty the car was. Sam demanded the keys – “If you don’t know who you are, I can’t trust you to know how to drive, Dean.” – and got them back to the motel in no time.

“Things are moving pretty quickly, aren’t they Sammy?” Dean asked with a wink as they stepped into the room.

“It’s Sam,” Sam spat back, pushing Dean toward one of the beds. “You are sitting here. I’m going to figure out what the hell happened.”

Dean watched as Sam moved around the room, trading his too-big flannel for one of Dean’s slightly smaller ones, gathering a book and a laptop, as well as putting away his and Dean’s guns for a smaller handgun that would fit his now feminine fingers better.

“You will not leave this room until Cas gets here. He’ll help us figure this out.”

Dean seemed to like being bossed around even without his memories of Sam, as he nodded obediently and accepted the television remote.

“My number is in your phone, but Cas will be here soon.” Sam turned for the door, opening it. He looked back at Dean sitting on the bed. “Do not leave.”

Dean grinned. “Yes, ma’am.”

Sam nodded and closed the door, leaving Dean to his television watching.

Dean flipped the TV on, but didn’t really look at what was on screen. Instead he looked at his lap, smiling mischievously.

“You like being ordered around, dontcha boy?” Dean moved more fully onto the bed, stretching his legs out in front of him. He shifted his semi-hardness in his jeans to be a little more comfortable before pulling out his phone. It unlocked automatically, and he distracted himself by scrolling through texts and contact numbers, trying to remember something…anything.

When the door to the motel opened again, Dean hadn’t triggered any memories. He looked to the door, expecting to see Sam’s feminine but tough form there, but instead was met with a handsome man in a trench coat, blue eyes piercing even across the room.

“Uh…” Dean said eloquently, sliding off of the bed to stand. “Are you Cas?”

The man closed the door and walked toward Dean, stopping altogether too close. Blood flowed south to Dean’s cock in a pique of interest and he filed that reaction away with a smile.

“My name is Castiel,” the man said, his voice low and gravelly. Dean shivered, his body still a bit sensitive from being around Sam and responding strongly to the timbre. “You do not know who I am?”

Dean shook his head, shrugging. “I don’t know who _I_ am, man. But that Sam chick told me you were coming, so I took a guess.”

Castiel nodded, reaching a hand out. He touched Dean’s forehead, a warmth spreading from the place Castiel’s fingertips met skin. Dean didn’t stop the pleased moan that bubbled up from his throat.

Castiel’s eyes widened in response, pupils dilating. Dean recognized that look and decided to grab the reigns of his amnesia and run with it.

He stepped forward, closing the remaining space between them, and planted his lips on Castiel’s. The other man froze for a second before his hand moved from Dean’s forehead to cup his jaw. Dean smiled into the kiss and deepened it, letting his hands find Castiel’s waist.

They kissed for a minute, Dean trying to remember – to learn – the taste of the man. When he needed to breathe, he pulled back, but didn’t let go of Castiel’s body.

“I take it we’ve done this before?” Dean asked, hopeful. Castiel tilted his head, considering Dean’s words.

“Sort of,” Castiel replied. Dean gave him a confused look, which prompted Castiel to expand on his answer. “We’ve, ah, been intimate in ways other than this, but haven’t ever ‘made out’ in quite this way before.”

Dean rolled his eyes at the one-handed air quote that Castiel used, sure that if he knew the man he’d made fun of the gesture before.

“Well, we should continue, then, shouldn’t we?” Dean asked, not waiting for an answer before surging forward again.

This time, he walked forward as well, backing Castiel up to the motel room door. Dean pressed up against the lithe body, his erection swelling with each swipe of their tongues.

Castiel moaned, a deep rumble that sent zings of pleasure through Dean’s body. He slipped his leg between Castiel’s, getting an explicit feel of how much Castiel was enjoying himself.

Dean began moving his hips, pressing their bodies as closely as he could while also getting some delicious friction. Castiel’s hands slid from Dean’s face down his shoulders and back until they squeezed at Dean’s ass. 

Yep, whether Dean could remember it or not, he knew that his ass was on board for whatever was happening.

But there were clothes – just way too many layers – and Dean was desperate and impatient. Screw getting their clothes off, they could do that some other time. Right now he needed to just…

Dean shifted the angle of his hips slightly so that he could slide his hard cock along Castiel’s, in the crook of Castiel’s hip. They panted into one another’s mouths, kissing when they could but really just sharing air and saliva, a wet, hot, and messy connection.

“Oh my God, Cas-“ Dean most certainly _didn’t_ whine, just before painting the inside of his boxers like a teenager. He bit his lip and let his head fall back as Castiel guided the movement of their hips so that he could come, himself.

Once Castiel had growled Dean’s name deliciously as he came, their movements stopped and the room was silent, save for their heavy breaths. Dean’s head leaned forward so that he could nuzzle Castiel’s neck. He smelled of sky and trees and a summer’s breeze, and Dean wondered how someone could wear a trench coat and jacket and _not_ smell of sweat, especially after a hot and heavy make-out, but right now he really didn’t mind.

Dean’s phone ringing across the room brought them both to their senses and Dean pulled away reluctantly to answer it. He’d have to have some pillow talk with Castiel later, it seemed.


	10. Chapter 10

**Notes for the Chapter:**

> This chapter covers the Pegging square for SPN Kink Bingo and the Smut square for Heaven & Hell Bingo. (Wincest this chapter, y'all! And yeah, more Dom!Sam and sub!Dean, so don't like don't read.)

Sam was heading back to the motel, she – he? – told Dean on the phone, so Dean slipped into the bathroom to clean up. When he came back out, Castiel was sitting stiffly at the table.

“Do you, ah, need to clean up?” Dean asked awkwardly. Castiel tilted his head.

“Thank you, Dean,” Castiel replied, “but I am fine.”

Dean harrumphed. “Okay, Cas, whatever you say.”

Before the conversation could continue, the door opened and Sam walked in. Castiel stood.

“The witch has completely vacated the building. No sign of where she went, and I didn’t find any spell-casting items that would explain our…” Sam motioned between herself – himself? – and Dean, “…situations.”

Castiel nodded. He walked toward Sam and put his fingers on Sam’s forehead, just as he had done with Dean upon arrival. Dean tilted his head, wondering what was going on.

“I cannot seem to fix you myself,” Castiel said as he pulled his hand away. Sam sighed, but didn’t look surprised. “Allow me to search the town, find the witch. I’m sure I can get her to reverse the spells placed upon both of you.”

Castiel looked to Dean as he finished talking, an undecipherable look on his face. Dean grinned. “Sounds great, Cas, I’m sure you can find that witch in no time.”

Both Sam and Castiel looked at Dean then, making him feel a bit awkward. “I mean, you seem…capable?”

Sam rolled her eyes and went to the chair that Castiel had been sitting in. She opened the laptop and started typing away. “Call if you need backup, Cas.”

Castiel nodded, heading for the door. “Of course.”

With that, Sam and Dean were alone in the motel room.

Dean stood there awkwardly for a minute, wondering what he should be doing. Sam was concentrated on the laptop, the television had nothing interesting on it, and frankly Dean was completely confused about what was going on.

Sam finally looked up to see Dean’s uncertainty.

“Dean, stop being awkward and sit.”

The commanding tone of Sam’s voice zinged straight to Dean’s apparently not-too-tired dick, which twitched in interest.

_Down, boy_, he thought to his dick while his mouth answered, “Yes, ma’am.” He followed Sam’s order without hesitation. Once Dean was seated across from Sam, he saw the flare of Sam’s pupils.

_Oh, so you like ordering me around just as much as I like being ordered around?_ Dean thought to himself, planting a smile on his face that he was sure was flirty. 

“What would you like me to do now, ma’am – I mean, Sam?” Dean asked, taking note of the sharp inhalation at Dean’s purposeful slip-up.

Sam cleared her throat, looking back at the laptop. Dean stayed still, awaiting orders like he’d done it his whole life.

Who knows, maybe he had been following Sam’s orders his whole life.

“Um,” Sam fumbled, reaching for a few books on the table. “Just, read.” Sam shoved a large, very old tome in front of Dean, who opened it somewhere to the middle. Sam went back to the laptop as Dean started to read, but he couldn’t concentrate.

Every nerve was on edge waiting for Sam to tell him what to do. Sure, Sam had told him to read, but he had a feeling Sam didn’t expect Dean to actually _read_.

As casually as he could, Dean leaned back into his chair, rubbing his hand along his chest and belly as though to relax. He made sure, though, that his shirt rode up just enough to draw attention, and…

“Dean!”

Dean’s eyes went from glazed over “reading” to Sam’s face. Her eyes were narrowed, as though she knew exactly what Dean was trying to do.

But it worked, didn’t it? Dean got Sam’s attention in less than two minutes?

“Yes, Sam? Do you want me to do something else?” Dean asked sincerely. When Sam didn’t answer right away, he continued. “I’ll do anything you want, just tell me.”

Sam mumbled something, too low for Dean to make out. Dean leaned forward, threading his fingers together in a prayer-like motion above the table. “Anything you want,” Dean repeated.

Dean was convinced Sam didn’t even try to hide the dilation of her eyes for him to see, and Dean grinned. His dick was interested, that’s for sure, and was trying its best to fill again, so soon after his orgasm with Castiel.

At the thought of Castiel, Dean almost faltered, but when Sam stood Dean didn’t let himself become distracted in his thoughts.

“Do you really want to do this, Dean?” Sam asked lowly. Dean swallowed and nodded. “You don’t even have your memories,” Sam continued, reaching a hand out to cup Dean’s face gently, “but still you are such a good boy for me.”

Dean bit his lip, nodding again.

They were frozen for a minute before Sam nodded sharply. “Alright then. Strip, bed, all fours.”

Dean went into motion without hesitation, a fleeting feeling telling him he had followed those three orders many times before. In just a minute, he was on the motel bed, baring himself to Sam.

Sam wasn’t paying attention to Dean, though. She was digging through a bag, her back to Dean. He heard rustling of plastic, the clinking of a belt, and some other confusing sounds. It didn’t matter, though, because he would wait as long as it took.

Sam moved to put something on the end of the bed, a hand falling to Dean’s ass in a light smack. “Safeword?” Sam asked, casually like she’d asked a thousand times before.

“Uh…” Dean replied, having no idea what to say. Did he have a safeword? Surely he did, but he had no memory of one.

“Oh,” Sam said quickly, realizing that Dean wouldn’t remember his safeword. “It’s usually Poughkeepsie, but you can use anything you’d like.”

Clothes rustled behind him but Dean stayed looking forward. “Poughkeepsie works for me, yeah.”

Dean heard the snick of a bottle and then there was cold liquid drizzling down his crack. He jumped slightly, but pushed back into Sam’s hand as it followed the drizzle. “So needy, even without your memories, Dean,” Sam commented, fingers thin and long. “This will be different, that’s for sure, but I’ll make you feel real good.”

Dean groaned in response as one of Sam’s fingers slipped easily into his hole, confirming to himself that he had done this before, and probably recently. His ass didn’t protest in the least as Sam started pumping the finger in and out, even when a second and third was added it wasn’t uncomfortable.

It also didn’t hurt that Sam was obviously a pro at taking Dean apart, piece by piece.

Soon Dean’s head was smushed into the pillows and Sam had four fingers pumping inside of him. Sam’s free hand was rubbing Dean’s lower back, keeping him grounded. It squeezed gently as Sam’s fingers left Dean’s hole, giving his prostate a gentle nudge on their way out.

“Wha-?” Dean protested, looking over his shoulder at Sam for the first time.

His eyes bulged.

While Dean was waiting, Sam had obviously worked quickly. All she had on was a white, men’s undershirt, which bunched slightly as it ended above a homemade strap-on. Sam had taken a couple belts and an impressive dildo and strapped them to her hips so that the flesh-colored erection stood out as if it were her own.

“You okay, Dean?” Sam asked, rubbing his lower back still. She was smiling and drizzling more lube onto the dildo, coating it with her free hand.

Dean swallowed. “Fuck, yeah. Green light, for sure.”

Sam’s smile widened. “It’s not as big as you’re used to, you know…or I guess you don’t know, but it’s not as big as you’re used to. Just let me know if anything is…off.”

Dean nodded before planting his head against the mattress again. He felt Sam press the dildo to his willing hole and push forward, Dean’s body taking it like the thing was made for him.

Who knows, maybe it was made for him.

All thoughts left Dean’s mind as Sam started to move, her hands holding Dean’s hips as she thrust the dildo in and out of Dean. It took her a minute to get a good angle, but then she was hitting Dean’s prostate with every movement, his cock definitely interested and willing to come again.

Dean didn’t realize the noises that he was making until Sam leaned forward to squeeze his shoulder. “It’s okay, Dean,” Sam cooed. “Come for me, come on my cock.”

Maybe it was how riled up he was, maybe it was Sam’s feminine voice in his ear, maybe it was just the way Sam said ‘cock’, but right then Dean was coming all over the bedspread, his vision going white with pleasure.


	11. Chapter 11

**Notes for the Chapter:**

> This chapter covers the Fingering square for SPN Kink Bingo and the Free Space for Dean and Sam Bingo.

****Dean felt gooey as Sam cleaned him up, careful and gentle. It was nice, having someone taking care of him. It felt familiar, even if he didn’t remember if it had happened before.

When Sam came back to the bed, she encouraged Dean to the crook of her arm and he rested his head on her shoulder. She raked her fingers through his hair, an intimate gesture that had Dean reaching for her as well.

He fiddled with the fabric of the white t-shirt, Sam’s body warm underneath.

“So you’re not actually a chick?” he asked quietly. “And that happened at the same time I lost my memory?”

Sam breathed out slowly; Dean guessed she was trying to figure out what to say. “Yeah, I’m not a chick. This is a hell of a lot stranger than most things we get into, Dean, so I’m sorry you don’t have your memories for it. Let’s just say that we usually do all that stuff without the help of the dildo…although sometimes it’s nice to play with.”

Dean grinned, thinking of a few ways two guys could use a dildo. His fingers trailed down Sam’s t-shirt. “So…” he started again as his fingers approached the bottom of the shirt, “all this equipment is new to you?”

Sam shifted, watching Dean’s fingers as they met skin. Sam’s oversized shirt had been hiding her modesty, but Dean began dragging it upward to reveal Sam’s new body.

“New in that it hasn’t ever been mine, not new that I don’t know the ins and outs…” Dean understood – Sam was bisexual, had been with guys and girls. Dean felt in his bones that he was the same, even if he didn’t remember any previous encounters.

He moved slowly, watching as Sam’s body opened up for him. Sam’s shirt was now resting along her belly button, and when Dean’s hand nudged Sam’s thigh, her legs fell open.

There was a tuft of dark hair just below the creases left by the strap-on belts, and Dean scratched his fingers into it. Sam’s breath hitched as Dean’s fingers moved down to find wet pussy lips. His middle finger pressed into the warmth, paying attention to every response Sam gave him.

He lifted his head off of Sam’s shoulder and pushed himself up on his elbow, hovering next to her slightly. Sam’s eyes were blown, a look of arousal and curiosity in them. “Let’s see how all this works, shall we?” Dean asked. Sam nodded, licking her lips.

Dean’s middle finger slipped along Sam’s lips until it found her entrance, dipping inside. It was warm and inviting, but Dean was almost more interested in Sam’s response. He could tell that she was curious, making mental notes of how things felt, but was also going to be easily distracted by her educational interests.

Dean pumped his finger a few times before sliding it out and lining his ring finger up with it, the two diving inside once more. Sam’s legs fell open a bit wider, easing the way for Dean to play.

Sam bit her lip, stifling a pleasured sigh. Dean didn’t want Sam holding back, so he leaned in to release Sam’s lip with his own.

Even though Dean’s fingers were the ones guiding this exploration, Sam’s tongue was still dominant in the kiss. Dean fell into the kiss as his hand continued its pumping, stretching and exploring Sam’s inner depths.

“De-“ Sam sighed into the kiss. Dean pulled away slightly, looking down at Sam. “I need…oh…I need…”

Dean smiled, shushing Sam gently. “Don’t worry, I got you.” He kissed Sam once more before shifting to move down Sam’s body, kissing the fabric of the t-shirt. He found the swell of Sam’s breast and gently bit at the nipple through the fabric, earning a back-arching groan in response. Dean continued moving down until his kisses met skin.

He shifted to lay between Sam’s legs, looking up her body to see Sam’s eyes on him. “Let’s see how this really feels, yeah?” Dean asked before he leaned in.

His tongue licked around Sam’s entrance, where Dean’s fingers were still two knuckles deep. Sam shifted, assessing the new feeling.

Dean’s tongue tasted Sam’s inner pussy lips a bit longer, her sweet tang addictive. When he couldn’t hold back anymore, he moved higher in search of the magical nub he knew was there.

When he found Sam’s clit and lapped at it, Sam’s knees closed in around Dean’s shoulders automatically. He used his free hand to spread them back out and went to work.

His fingers continued a steady in-and-out, but now his tongue danced with Sam’s clit. He read every response she gave him, figuring out exactly which flick, swish, or press worked best. Soon Sam was crying out, begging for more. Dean couldn’t stamp down the swell of pride filling him at Sam’s desperate responses to him.

He added another finger and searched inside for her pleasure spot, finding it quickly and stroking it relentlessly from the inside as he sucked and lapped at Sam’s clit until she was clamping down on his fingers in orgasm. Dean kept going until Sam was pushing him off, sitting up to pull him into a kiss.

Sam’s taste was shared between their tongues until it was all but gone, both of them breathing heavily. Their foreheads rested against one another as their heartbeats calmed.

“Well.” Dean chuckled. “That was educational.”

Sam smacked his arm and got out of bed, heading for the bathroom. Dean watched as she closed the door behind her before he climbed under the covers, exhausted in every way.


	12. Chapter 12

**Notes for the Chapter:**

> This chapter covers the Role Play square for SPN Kink Bingo. (1950's family-type role play, Sastiel!)

Sam didn’t bother the soundly sleeping Dean when he came back out of the bathroom. Instead she sat in the other bed, laptop settled in next to her.

She didn’t notice how much time had passed before the door opened, Castiel entering. He looked from the sleeping Dean to Sam and smiled.

“Honey, I’m home,” Castiel sing-songed, making Sam laugh. They’d spent some of their free time recently watching shows like I Love Lucy, and Castiel enjoyed quoting the show when Dean wasn’t around – Dean only made fun of them for it. She closed the laptop and stood, walking toward Castiel.

Smile on her face, Sam reached for Castiel’s trench coat, taking it off of his shoulders like a 1950’s wife might for her husband.

“And how was work today, sweetie?” Sam joked, throwing Castiel’s coat over the back of a chair before reaching up to primp her hair like it was styled. Castiel watched the movement closely before glancing back at Dean.

When Castiel looked back at her, Sam realized that Castiel seemed to be very into their act, more so than usual.

“Oh, you know,” Castiel said, taking a step toward Sam, “business as usual. Found a witch, interrogated her, then got rid of her. Just a normal day at the office.”

By the time Castiel was done speaking, he and Sam were breathing the same air. Sam shivered at the closeness, finding himself not at all uncomfortable and a bit surprised at that.

“Oh?” she asked. “And what did the witch say about…” Sam motioned at her body and toward Dean in the bed.

One of Castiel’s hands reached out to settle at Sam’s waist, through the t-shirt. Sam stopped breathing.

“Should wear off pretty soon,” Castiel answered, eyes watching Sam closely. “Both spells were timed, no need for a counter spell or potion.”

Sam nodded, swallowing. “That’s good,” she said. She saw something past Castiel’s shoulder and had an idea. “Since you had such a successful day at _work_,” Sam continued, squeezing Castiel’s forearm as she slipped from his grip and past him, “let me make you an afternoon cup of coffee.”

Castiel turned to see Sam holding the motel room’s coffee pot in one hand, a mug in the other. He could almost see her, in his mind’s eye, wearing a pretty, knee-length dress with a petticoat underneath – maybe pink with white polka dots and a tie around the waist, or perhaps dark blue with a bow at her waist – instead of the too-big men’s t-shirt she was currently wearing.

The thought of Sam dressed like a 1950’s housewife pushed Castiel even further into the charade they had going and he grinned like a Cheshire cat. “That sounds lovely, dear,” Castiel replied, sitting in the chair that was holding his coat.

Sam’s eyes widened before she smiled and turned to the coffee maker, setting it to brew. She didn’t really know what was happening – was it because she was still riding the high of Dean giving her a very _female_ orgasm, or was this just because of Castiel – but whatever it was, Sam was, interestingly enough, enjoying it.

The coffee was ready fairly quickly, and Sam poured the cup out and placed it on a saucer. She laid it in front of Castiel, sitting across from him and crossing her legs.

Castiel never took his eyes off of her as he drank from the mug, the warm coffee soothing his body unnecessarily. He set the mug down and reached a hand out toward Sam.

Sam took it, letting Castiel help Sam up and pull her close.

“Isn’t it common to be welcomed home from work with a kiss as well?” Castiel asked, only a small catch in his throat giving away his nerves.

Sam blushed – visibly blushed – before she nodded. “I suppose so,” she replied. She tilted her head toward Castiel but let him take the lead, the kiss a barely-there brush of skin.

They pulled back slowly, goofy grins on their faces. The day’s events had certainly opened both of their eyes to quite a few new possibilities, now they would only have to figure out what to do with themselves.


	13. Chapter 13

**Notes for the Chapter:**

> For the Cockwarming square of SPN Kink Bingo and the Free Space of Heaven & Hell Bingo. Sastiel!

“So this is new,” Sam commented, motioning between herself and Castiel. Castiel took a step back, misunderstanding. “Not that I don’t like it,” Sam continued, pulling Castiel back in for another kiss.

Castiel breathed heavy against Sam’s mouth, nodding his head back and forth as he sorted his thoughts. “Yes, I suppose it is new,” Castiel agreed. He looked over at where Dean was still sleeping in the bed as he continued speaking. “I seem to be… waking up to my more primal instincts as of late.”

Sam looked at Castiel with a teasing grin, catching Castiel’s eye again. “Do I want to know what else you’ve been doing lately, Cas?” she asked, before doubling over with a moment of queasiness.

“Sam, are you alright?” Castiel asked immediately, grabbing at Sam’s shoulders to steady her. She straightened up again to give Castiel a full view of her face…which was beginning to change shape.

Castiel knew what was happening. “You’re changing back. Here, sit on the bed, you will probably be dizzy and weak for a minute while the change is happening.”

Sam let Castiel guide him to the empty bed, sitting carefully as her body started changing back to normal. The long hair began to suck back into her scalp, until it was just above shoulder-length. Her face shape changed back to a strong, stubbled jawline, and her entire body seemed to grow in size – shoulders broadening, arms and legs lengthening, breasts flattening to form pecs instead.

Suddenly it was Sam, the man, sitting on the bed next to Castiel, where Sam the woman had just been.

Sam, the woman who had only been wearing a too-large plain t-shirt, was now Sam, the man, whose t-shirt fit him as a man’s t-shirt should…and no longer covered up anything below the waist.

Sam didn’t have time to do anything about it, though, before Castiel’s eyes were drawn to Sam’s genitals. Sam had always heard, both from Dean and other partners, that he was impressive in every way, whether hard or soft. He had a drool-worthy cock, and now Castiel was staring at it.

Without Sam’s permission, his dick twitched at the feeling of eyes on it.

Castiel licked his lips at the movement before his eyes snapped back up to meet Sam’s.

“I, uh,” Castiel started, obviously feeling awkward. “I apologize, I am crowding your personal space.”

Castiel moved to stand up, but Sam’s strong hand on Castiel’s shoulder stopped him. Their conversation, from before Sam’s change back to normal, resurfaced in Sam’s mind.

“We were talking about your more…primal instincts?” Sam prompted, his hand sliding from Castiel’s shoulder down his back until it rested on the bed behind Castiel. Sam leaned in slightly, watching Castiel’s pupils dilate and his Adam’s apple bob as he swallowed deeply. Castiel glanced over at Dean’s sleeping form again, before looking at Sam with wide eyes. Sam smiled at Castiel’s tell – obviously something had happened between Castiel and Dean. He let that thought roll around in his mind for a minute and found himself perfectly okay with the idea of Castiel and Dean having been together.

Heck, it even interested him a little bit.

His cock bobbed in agreement.

The motion drew Castiel’s eyes again, and this time Castiel didn’t look away. “You have a very attractive penis, Sam,” Castiel said quietly. Sam saw Castiel’s fingers twitch slightly on his leg. “It is truly something to be proud of and enjoy.”

Sam grinned, having an idea. He’d let Castiel take the lead, of course, so he shifted. Sam laid back on the pillows, propped up enough that he was still sitting up slightly. He let one of his legs fall outward, spreading himself out for Castiel to see.

“I do enjoy it quite a bit, Castiel,” Sam admitted. “So do others…”

Sam let that thought hang in the air between them. Castiel looked from Sam’s face to his semi-hard cock before his lips twitched upward in a tiny smile.

“I am sure it’s quite enjoyable, if you wouldn’t mind…” Castiel finally said. Sam nodded, motioning for Castiel to do what he wanted. Castiel stood, taking off his suit jacket and throwing it to the chair with his trench coat, also loosening his tie. He slipped his shoes off before climbing onto the bed, finding himself between Sam’s legs.

“I, um,” Castiel stammered, feeling a bit awkward.

Sam sat up, grabbing Castiel’s face and kissing him. The kiss was different, now that Sam was a man again, but neither of them noticed or cared. It was Sam and Castiel, and that’s all that mattered in the moment.

“Do what you want, whatever you want,” Sam insisted. “I’m all yours.”

Castiel nodded, watching as Sam settled back again. He eyed Sam’s cock, his mouth watering. “I think…” Castiel started. “I think I just want to hold you for a while.”

Sam nodded. To his surprise, instead of Castiel reaching out with his hand, Castiel leaned down to gather Sam’s semi-hardness in his mouth. Sam was still soft enough that he was pliable and Castiel was able to get nearly all of Sam into his mouth, smushed as it was.

Sam watched with wonder as Castiel rested his head against Sam’s thigh, holding Sam’s cock in his mouth with no other movement. His tongue was still, his jaw wide open to accommodate. The warmth and wetness was nice, calming even, and Sam was surprised at himself that he wasn’t getting harder by the second.

It was refreshing, really, and Sam relaxed into the pillows to lazily watch Castiel as his eyes fluttered shut, mouth stuffed with Sam’s dick.

Sam wasn’t sure how much time passed before they seemed to wake from their daze, or rather Castiel nudged them out of it. Very slowly and gently, Castiel’s tongue began to press against Sam’s cock until the blood started filling, Sam’s erection growing steadily in Castiel’s mouth.

Sam had been so relaxed and calm that the change in events, from a half hour or more of just resting, warm in Castiel’s mouth, to Castiel actively giving Sam a blowjob had him coming down Castiel’s throat sooner than he expected.

Castiel smiled when he pulled back, rubbing his jaw with one hand as it popped. “That was nice,” he said. “Thank you, Sam.”

Sam reached for Castiel, pulling him up the bed to lay next to him. Sam kissed him, tasting himself in Castiel’s mouth. “It was more than nice, Cas. I should be the one thanking you.”

Castiel shook his head, but let Sam maneuver them both until they were laying under the covers, Castiel’s head on Sam’s shoulder.

For a fleeting moment Sam realized this was the same position he and Dean had been in mere hours before (when Sam had been _much_ more feminine), but then he was falling asleep, a relaxed angel in his arms.


	14. Chapter 14

**Notes for the Chapter:**

> This chapter is for my Polyamory square for SPN Kink Bingo and polyamorous square for Sam W Bingo. No smut!

Dean’s head was pounding and he reached for it, massaging his temples before he even opened his eyes. He was met with the ugly ceiling of their motel room, and everything came rushing back to him.

Everything, like _everything_. He had his memories back, plus the memories of everything that had happened since the witch zapped him and Sam.

Sam.

Dean sat up quickly, looking around the room. His eyes landed on the other bed, where a very masculine Sam lay. But to Dean’s surprise, Castiel was curled up against Sam’s body, sleeping tucked under Sam’s arm.

Dean frowned.

A strange feeling pooled in his belly, one that he wasn’t sure if he was comfortable with. He thought to himself for a moment, but couldn’t pinpoint what the feeling was. 

He and Sam, while always having their thing, had also always agreed that they weren’t exclusive. He loved Sam and would do anything for him, including die for him, but he also just wanted Sam to be happy. If that happy came from other people sometimes, so be it.

He and Castiel… That was a whole monster that Dean had just started to see creeping in from the rafters. After the thing with the accent at the convenience store, then the incredible blow job in the car, and ending with the groping and making out and coming in his pants like a teenager while he rutted Castiel up against the door when he didn’t even _remember_ their history…

Fuck, Dean had a serious thing for the angel.

But now Sam and Castiel were acting all snuggly over there in the bed – had something happened?

Was Dean okay with that?

He shook his head, mind whirring. The motion seemed to alert Castiel, who Dean should have realized wasn’t truly asleep. 

“Dean?” Castiel said, drawing a deer-in-the-headlights gaze from Dean and waking Sam. “Do you have your memories back?”

Dean moved to stand before realizing that he was still naked from his and Sam’s earlier escapades. He grabbed at the blanket and pulled it tighter around his waist.

Sam and Castiel both sat up, waiting for his answer. Dean’s eyes moved between the two of them before he looked away, rubbing his hands through his hair.

“Yeah, I’ve got my memories back. And looks like Sam’s got his body back, too.” Dean looked back over at Castiel. “Didja get the witch bitch?”

Castiel nodded. “Yes, I found her and interrogated her before taking care of her. The spells were timed, so it was only a matter of waiting until the two of you timed them out.”

Dean nodded, but didn’t respond again. Sam shifted on the bed, reaching toward a duffle to grab a pair of boxers and put them on. Dean’s eyes widened with the knowledge that Sam had been snuggling with Castiel in that bed with _no boxers on_.

“Dean,” Sam said gently, crawling onto Dean’s bed. Dean recognized that tone of voice. That was Sam’s _we need to talk_ tone.

“This is weird, isn’t it?” Dean blurted out, standing and taking a blanket with him, tucking it around his body so he could pace the room. “I mean, you and me, Sammy, we’re already fucking weird. Not a bad weird, of course, ‘cause I wouldn’t have it any other way, but weird all the same.”

Sam nodded, understanding Dean’s meaning. Dean turned to Castiel.

“And then you ‘n’ me lately, it’s like…” Dean paused, grasping for words. He gave up. “I don’t fucking know. Like I’m on fire and you’re the ice water that puts me out. But also you’re the one who sets me on fire, right?”

Castiel’s head tilted in confusion, but Dean didn’t explain more.

“And then the two of you now, I guess?” Dean stopped pacing, standing right between them. “I mean, there’s no rhyme or reason why I should be mad. And it’s weird, ‘cause I’m not mad. In fact, it kinda makes me happy in a way, because it makes me feel less…I don’t know.”

The room was suddenly quiet, with the end of Dean’s rant and pacing. Castiel didn’t know what to say, and Sam chose his next words very carefully.

“Dean,” he said quietly, drawing both of their attentions. “Have you ever heard of a polyamorous relationship?”

Dean squinted. “Isn’t that what people say when they’re cheating?”

Sam shook his head, laughing. “No, not at all. Not if they’re using it correctly. A polyamorous relationship is when three or more people are in a relationship, all together. Everyone with everyone, feelings all around. There are many types of polyamorous relationships, but,” Sam paused, looking over at Castiel for a moment, “I think the three of us might benefit from one.”

Dean sighed, the idea rolling around in his head. “You mean, you want to be in a relationship with me _and_ Castiel?”

Sam looked over at Castiel, who was eyeing the brothers thoughtfully. “If everyone is interested, then yes. If there are any hesitations, we should talk more about it at a later time.”

Dean was nodding before Sam stopped talking. “I’m interested. I’m definitely interested.”

The brothers looked at Castiel.

A million thoughts were going through Castiel’s mind, but at the forefront of all of those thoughts was the taste of each of them on his tongue. He might not know exactly what he was getting himself into with the Winchesters, but he was willing to give it a go.

Castiel nodded once. “Yes, I am interested in a polyamorous relationship with the two of you.”

Dean clapped his hands together in excitement, the blanket sliding down his body some. He grabbed at it quickly, making Sam laugh.

“Stop being awkward, let’s go home.”

“Yes, ma’am,” Dean quipped, diving for his duffle bag and clothes and dodging the pillow Sam threw at his head.


	15. Chapter 15

**Notes for the Chapter:**

> This chapter is for the Voyeurism square for SPN Kink Bingo, the Caudaulism square for SPN Poly Bingo, and the Free Space for Sam Winchester Bingo.

The trip back to the bunker was as normal as it could be. 

Dean played his happiest cassette tapes – not that Sam or Castiel pointed that out to him – and sang loud enough that even Castiel asked him to give it a rest. 

Sam played games idly on his phone or watched the passing scenery, making comments every once and a while that he knew would ruffle Dean’s feathers and earn himself a, “Shut up, Sammy.”

Castiel sat in the backseat, floating in and out of conversations and generally just…smiling. He didn’t need to ride in the Impala, he could have met the boys back at the bunker, but he enjoyed the quality time they were spending together.

Things felt very normal.

When they were back at the bunker, bags dropped off at their rooms and beers in their hands at the kitchen table, the whole ‘polyamory’ thing sank back into Dean’s mind.

“So how does this work?” Dean finally said, after sitting for almost ten minutes in a semi-comfortable silence. Sam shifted.

“I think the important thing is that we check in with each other, make sure everyone stays comfortable with things.” Dean nodded, agreeing. The last thing he wanted was for Sam or Castiel to hate him, or each other, because of something someone did.

“Also,” Sam continued, “I think it’s important that we nurture each relationship in this. It’s not just a two-way street anymore. It’s a crazy intersection with three couples and one poly. There should be a balance, and I’d like to work to keep the balance.”

“Two plus two makes three, right?” Dean asked, voice teasing. Sam rolled his eyes. 

“Yeah, sure.”

Castiel nodded, and the three of them took a swig of their beer simultaneously.

“So I was thinking about tonight,” Sam said. Dean was suddenly nervous. Should he have been thinking about tonight, too? Was Castiel thinking about tonight? What was Sam thinking?

“I’d like to, uh…” Sam blushed. Dean grinned, excited for whatever Sam was thinking if it was making him nervous. Sam took a deep breath and straightened his back, a tell-tale sign of his dominance coming out to play. “I’d like to watch the two of you, maybe tell you what to do, a bit.”

Dean looked over at Castiel, who nodded at Dean. “You don’t want to get in on this, Sammy?” Dean asked, drinking some more beer.

“Oh, I’ll be in on it,” Sam replied, giving them a teasing grin. “But I want to let you guys do the touching for a bit, at least.”

Dean drained his beer, standing. “Sounds like a plan. Meet in Sam’s room in 30?” He didn’t wait for a reply before he left the room, eager to clean himself up.

A half hour later, Sam was inviting Dean and Castiel into his room. They stood there in an awkward triangle for a moment before Sam took the lead. He grabbed Dean’s arm, pulling him close for a kiss. The familiarity of it relaxed them both, their breathing growing heavy from just the clash of tongues.

Sam broke the kiss, though, leaving a whining Dean to turn on Castiel. He kissed Castiel with the same fervor, if not the same familiarity. Sam had only kissed Castiel a few times in comparison to Dean, so this kiss was more exploratory.

When Sam pulled back from Castiel, Dean whistled. “Damn, that was hot,” Dean joked. Sam winked at him before motioning between Dean and Castiel.

“Your turn, and start slow,” Sam ordered. “No hands, no touching.”

He turned to sit in a chair he had a few feet away from the bed, spreading his knees and getting comfortable. Dean stared at Sam for a second before turning to Castiel. Dean smiled.

“Hey, Cas,” Dean greeted. Castiel’s lips turned up in reply.

“Hello, Dean.” Castiel’s voice was low and gravelly as always, but a long shiver went down Dean’s spine knowing that he could hear that voice whispering in his ear a lot more in the future.

Dean launched forward, knocking their noses together as he kissed Castiel. Dean had to grip his own thumbs in his fists to keep from grabbing at Castiel’s body, putting all his energy into his lips and tongue instead.

Castiel got with the picture fairly quickly, kissing Dean back with as much enthusiasm. Their teeth knocked together a bit before they got into a groove. They’d pretty much forgotten that Sam was in the room when he spoke.

“Dean, why don’t you help Cas out of his too-many layers?” Sam suggested. Dean broke the kiss long enough to glance over at his brother. Sam’s hands were flat on his thighs, but Dean could see the beginnings of an erection pushing a line down his jeans. Dean winked before grabbing the lapels of Castiel’s trench coat, pulling him back into a kiss and sliding the coat down Castiel’s shoulders.

His jacket was next to go, and Dean couldn’t help himself when he grabbed for Castiel’s tie and pulled them flush together. Sam watched as Castiel’s hands spread out to the side, obviously wanting to grab onto Dean but still following Sam’s orders of no touching.

“Cas, Dean’s got a great ass, don’t you think?” Sam said, smiling as Castiel reached for the back of Dean’s pants. To both Winchesters’ surprise, Castiel’s hands slipped inside of Dean’s back pockets, pulling Dean’s hips forward, flush against Castiel.

Dean groaned into the kiss, undoing the knot of Castiel’s tie and sliding it off to drop to the floor.

“It’s awfully nice for you to help each other with all those pesky buttons,” Sam suggested, and Dean and Castiel’s hands both moved to each other’s shirts. Soon the shirts were off and they were chest-to-chest, a hum of pleasure from Dean at the warmth of Castiel’s skin.

Castiel’s arms wrapped around Dean to pull him close, tracing up and down his spine affectionately. Dean shivered, his hips pushing forward.

Sam’s eyes raked across the picture in front of him, arousal swelling his cock uncomfortably. Pants needed to come off, now.

“Get the rest of it off, now,” Sam ordered, watching as Dean and Castiel’s frantic fingers freed each other of their pants and boxers. Sam undid his own jeans, sliding them down just a bit so that his erection wasn’t trapped anymore. He kept himself tucked in his boxers though, sure that he could keep control.

Dean and Castiel, on the other hand, were rutting together like teenagers. Sam watched their movements for a minute before giving his last order. “Dean, get the lube. Slick it all up and both of you fuck your fist, nice and tight.”

Dean went for the bedside table where he knew Sam kept their lube, pouring it onto his palm as he walked back over to Castiel. He drizzled a bit more onto their dicks, lined up nicely between their bodies, before taking them both in hand. 

Castiel’s arms went around Dean’s shoulders and he took steady breaths as Dean began pumping them together, the slickness of the lube easing the way for them to slide together. It was wet and hot and enough that Castiel had to claim Dean’s mouth in a kiss again, just to keep his voice down.

Sam almost wished he didn’t, because Castiel was making the most beautiful sounds. He gave up his self-control and took his own cock from his boxers, licking his palm to ease the gentle stroke of his own hand. The sight before him, Dean and Castiel enjoying each other, was more than enough to turn Sam on. They were both beautiful, but together? They were magnificent. A dream.

And they were happy, which made Sam happy.

Sam noticed the little noises coming from Dean that prefaced his orgasm, so he stopped stroking himself to concentrate on their pleasure. Dean’s hand sped up, chasing toward that edge, until finally he was spilling all over their stomachs, cocks, and his hand.

Castiel whimpered at the warmth, his hips moving to pump harder against Dean’s dick and hand to find his own orgasm, which came less than a minute later. 

They leaned on one another, legs wobbly, as they kissed a bit more, slower this now. They squished the mess between them, needing as much contact as possible.

Sam’s heart couldn’t have been more full at the sight.


	16. Chapter 16

**Notes for the Chapter:**

> This chapter is for the Size Kink square for SPN Kink Bingo and the Poly Vee square for SPN Poly Bingo. Wincestiel.

Dean and Castiel finally stopped kissing, eyes closed and foreheads resting together as they stood in front of Sam, wrapped up in each other’s arms. Dean could feel Sam’s eyes on them, watching them, and he got an idea.

He leaned in to whisper something to Castiel, so that Sam couldn’t hear it. Before Sam could say a word, Dean and Castiel turned to face him, falling to the floor. Dean grabbed his t-shirt and wiped them both off a bit before they crawled over to Sam.

“We got to have our fun,” Dean said, grabbing at Sam’s jeans.

“Now you get to have some fun, too,” Castiel finished. Sam almost argued, ready to explain that he had quite enjoyed watching the two of them, but then Castiel’s hand was on his cock.

He pumped Sam a couple times before looking to Dean, who reached for Sam as well. Their fingers entwined as they started to jerk Sam’s cock together, moving in time.

“So big that even both of our hands don’t cover his whole cock,” Dean said quietly, sighing. Castiel nodded next to him.

“Such a beautiful, big cock,” Castiel continued. “There’s nothing like it, really.”

Sam’s head fell back and his hands grasped the air, the knowledge that both Dean and Castiel were working together to pleasure him overwhelming. With his head back and eyes closed, he didn’t have any warning for what happened next.

Dean and Castiel’s hands left him to be replaced with two tongues, dancing up and down his cock together. Every so often, one of them would moan things like, “So big” and “Can’t fit him in just one mouth,” making Sam groan. Sure, he knew he was larger than most, but the thought that Dean and Castiel both liked him because of his huge cock? That was hot.

Sam’s head lurched forward to watch as Dean and Castiel ravished his cock, sometimes kissing each other around his member. It was wet and dirty and hot as all fuck, and Sam could have come right then.

Then, as if they were speaking telepathically, Castiel moved up Sam’s cock to suck on his head while Dean moved down to mouth at Sam’s balls, just the way Sam liked it. Sam spread his legs as much as he could to give them room, but in the end it didn’t really matter.

“Good thing there’s plenty here for the both of us,” Dean said as he moved from one ball to the other. “More than enough, really. We’ll never get tired of this monster cock.”

The wet and heat and attention was all Sam needed to come, only giving a small word of warning before shooting into Castiel’s mouth. Dean licked up his cock to meet Castiel at the swollen head, Castiel opening his mouth to share some of Sam’s come. Sam watched as they shared open-mouth kisses, his spunk passing between them like candy.

His cock twitched like it wanted to come again at the sight.

When Sam had had enough, he leaned down to grab each of their heads, joining in on the kiss. It was uncoordinated and messy, but the three of them kissed back and forth for a minute more before they finally let each other go.

“You didn’t have to do that,” Sam said breathily.

Dean scoffed. “Of course we did,” he argued. “Do you think we aren’t invested in your pleasure, too?”

Castiel nodded in agreement, standing. He reached a hand out to both Winchesters. They stood, Sam losing the rest of his clothes, and let Castiel lead them to the bed.

“It’s just as you said earlier, Sam,” Castiel explained as he helped Sam into the middle of the bed. “We are all to nurture every relationship in this, no one gets left out.” Sam nodded, holding his arms out in invitation. 

Dean and Castiel both climbed into the bed on either side of him, their bodies turned in to snuggle.

“I could get used to this,” Sam commented. “Two hot as fuck guys on my arms, talking about how much they love my big dick?”

Dean smacked Sam’s chest, but it was playful. “Sleep, loser.” With a kiss for everyone, they closed their eyes to sleep, happy with their first day as a triad.


	17. Chapter 17

**Notes for the Chapter:**

> This chapter is for the Sub!Sam square for SPN Kink Bingo, and the Omorashi square for Sam Winchester Bingo. 
> 
> For those of you a bit hesitant about the Omorashi tag, I've separated the section with *** so that you can skip it if you want, with little affect to the work as a whole. But it's not terribly long - I'm not a huge fan of the kink so it's not a major part of this chapter.

Sam woke to the bed shifting next to him and he watched as Castiel left the room in the dark. Sam looked at the time – it was nearing four in the morning so he couldn’t blame the sleepless angel for wanting to get up and move around.

Now that he was awake himself, Sam rose too, leaving Dean snuggled amongst pillows and blankets to follow Castiel. Sam found him in the bathroom, just starting a shower.

“Hey, Cas,” Sam said, alerting Castiel of the company. Castiel turned and smiled, eyes looking Sam up and down.

Sam realized then that they were both still nude from the previous night’s events.

“I started to feel a bit uncomfortable with the leftover…” Castiel poked at his lower stomach, where Sam could see flakes of dry semen, “…you know, so I thought it would be nice to wash. Would you like to join me?”

Sam nodded, following Castiel into the shower stall. For a minute he watched Castiel stand under the spray, his hand gliding across his abdomen. Sam’s cock twitched slightly, a bit of interest showing.

Castiel must have seen from the corner of his eye, because he turned to Sam and reached for him. Sam let himself be pulled against Castiel, the warm spray of water falling over them both as Castiel tilted his head up for a kiss.

Sam’s hands explored Castiel’s arms and back as they tasted each other, their erections growing heavier between them with each moment that passed.When Sam’s hand reached down between them, aiming for Castiel’s cock, Castiel stepped back.

“I, um,” Castiel started, looking away sheepishly. “I need to urinate before…”

*******

Sam watched the shyness in Castiel, something that he wished he could get rid of. An idea came to mind, one that would put Castiel firmly in charge.

While he definitely preferred being the one in charge, Sam wasn’t too proud to be on the receiving end of things every once and a while, so he slowly sunk to his knees before Castiel.

“Go ahead,” Sam offered simply, closing his eyes.

Castiel’s eyes widened, realizing what Sam was telling him to do. One of his hands reached for his cock, feeling at the base and pointing it down slightly, below Sam’s chin.

Sam waited a minute before he felt a warm liquid, hotter than the shower water, hit his neck and chest. The shower washed it away quickly, and in less than a minute the stream ceased. Sam slowly opened his eyes to see Castiel blushing hard, but Sam only grinned.

*******

“No shame, Castiel,” Sam insisted. “We’re in this relationship, and I can be yours however you want me.”

“I – I thought…” Castiel stammered. Sam gave him a look that told Castiel to stop being so nervous. Castiel swallowed and started again. “You seem to enjoy being in charge, Sam. I didn’t realize you would enjoy other dynamics.”

Sam smiled, still on his knees looking up at Castiel. “I do enjoy being in charge, sometimes. But there’s something liberating about giving yourself and your freedoms to someone else, and I trust you with my freedoms, Castiel.”

Castiel smiled, a hand moving to cup Sam’s jaw. “Well, then. Open up.”

Sam glanced down to see Castiel’s cock fully hard, no distracting need for urination holding it back any longer. He licked his lips before opening his mouth, letting Castiel feed his cock into Sam’s mouth.

Castiel started slow, letting Sam get used to the taste and feeling of Castiel’s thickness, but soon he was holding Sam by the hair and fucking his mouth, not holding much of anything back.

Sam’s hands were on Castiel’s thighs, holding on for balance. His eyes watered and there was spit dripping from the corners of his mouth, but he wouldn’t want it any other way.

The way Castiel looked, taking what he wanted from Sam with his head tilted back…he was beautiful. Sam realized then, why their little relationship was going to work – not only did he have feelings for both Dean and Castiel, not only did he love to see them wrecked and wanting, but he also trusted them both explicitly.

Castiel started making a desperate little pant with each thrust into Sam’s mouth, and Sam knew he was getting close. He pressed his tongue harder against Castiel’s cock as he moved in and out of Sam’s mouth, and the extra pressure pushed Castiel to his orgasm.

Sam drank every drop of Castiel’s come, sucking at the organ until Castiel pulled away.

Sam stayed on his knees, looking up at Castiel and waiting for more instruction. Castiel gazed down at him for a minute, through a cloud of orgasmic glow, before offering his hand to help Sam up.

“Thank you, Sam,” Castiel said before kissing him gently. Sam smiled against Castiel’s lips. 

“Anytime,” Sam said, and he meant it. 

The two of them finished washing before drying each other off with fluffy towels and going back to Sam’s room. Dean had barely moved, and although Castiel didn’t need to sleep, he laid back down with Sam. Sam rested his head on Castiel’s shoulder, letting Castiel draw lazy scribbles on his back with his fingertips.

Sam was lulled back to sleep in no time, feeling content and cozy in Castiel’s arms. 


	18. Chapter 18

**Notes for the Chapter:**

> This chapter is for the Clothes Sharing square of SPN Kink Bingo, the Bed Sharing square for SPN Poly Bingo, and the Bed Sharing square for Dean and Cas Bingo.

To Sam’s surprise, the next time he woke up he was alone. He smelled bacon and coffee though, so he pulled on a pair of pajama bottoms and headed for the kitchen.

When he got to the kitchen, it was to see Dean pulling bacon from the frying pan and Castiel setting coffee mugs on the table. Sam caught Castiel’s eye and smiled, memories of their alone time in the shower still fresh on his mind.

Castiel walked over to Sam, getting up on easy tip-toes to kiss him. Sam’s arms wrapped around Castiel’s body and pulled him close, deepening the kiss.

“Hey there, don’t scar the bacon with your sex appeal!” Dean teased as he took the plate of bacon to the table. Sam and Castiel broke apart and grinned. They followed Dean to the table and grabbed him once the bacon was safely set down, smothering Dean with affection.

The older hunter slapped them away playfully. “It’s bacon time, not lovin’ time. Get your priorities straight, gentlemen.”

Sam rolled his eyes and took his seat. “Nothing about this situation is straight, Dean,” he quipped.

Dean stared blankly at Sam, unwilling to laugh at the joke. Sam was verified by a soft chuckle from Castiel, though, so he didn’t mind Dean’s sourpuss attitude.

It was as he was reaching for bacon that Sam realized that both Dean and Castiel were wearing his clothes. They’d both grabbed t-shirts from his dresser, and Castiel had gotten another pair of his pajamas while Dean stole a pair of boxers.

Sam was suddenly flushed with happiness, seeing the two of them in his clothes.

“What just got you all in a tizzy?” Dean questioned, recognizing the change in Sam’s emotions easily.

Sam blushed. “Nothing,” he said, stuffing an entire piece of bacon into his mouth. Usually he would have insisted they make something else – a spinach omelette or yogurt with fruit – but today he didn’t feel like starting an argument. 

No, today he wanted to eat breakfast with his partners and then take them back to his room.

That’s what he did, in fact. They finished the pile of bacon Dean had made fairly quickly and before Dean could disappear into the garage or somewhere else, Sam grabbed both of their hands.

“What?” Dean asked as Sam pulled them down the hallway.

“No work today, no cases, no research, no cars,” Sam listed. They got to his room and he nudged them inside, closing the door behind them. “This is new, and this is nice. I want to enjoy it a little longer before we get too used to it all.”

Castiel smiled, obviously understanding Sam’s sentimental nature easier than Dean. Instead of acquiescing, Dean headed for the door.

Sam stopped him with his body, pinning Dean with a non-negotiable look.

“You think you’re going to sleep in my bed, get up and put on _my_ clothes,” Sam couldn’t help the possessive growl that came with those words, “which you then parade around the bunker and cook breakfast in, and then tell me you’re not going to snuggle with me afterward?”

Dean’s eyes widened as he understood that not only was Sam being sentimental, but he was being quite Alpha-male possessive and it was ridiculously sexy. He smiled, hands finding Sam’s face to pull him in.

“Guess we’re staying in here for a while,” Dean said before closing the distance for a kiss. As they kissed, they fell toward the bed. Sam was lost in Dean’s mouth, so he didn’t notice when Dean reached out for Castiel.

Castiel climbed into bed behind Dean, spooning him as his hand explored up and down Sam and Dean’s bodies.

When Dean pulled back to breathe, Castiel leaned across him to kiss Sam in his place. Sam pulled at the collar of Castiel’s shirt – of _Sam’s_ shirt – for grounding. Dean watched from under them as they kissed, getting more and more aroused by the second. This time when Sam needed a breather, Dean turned his body between them to pull at Castiel.

Dean’s hips wiggled backward to find Sam’s, knowing exactly how to move against his brother to encourage a little fun. Sam’s hands found Dean’s hips and rutted forward, the thin layers of clothing not doing much to cover the warmth of Dean’s crack against the hard line of Sam’s growing erection.

Dean, though, was currently concentrated on Castiel. The angel was laying in front of him, looking absolutely gorgeous with his eager, aroused expression and wide eyes. Dean pulled him close, his hand sliding into the front of Castiel’s pants to palm at his cock.

“Dean-“ Castiel sighed, leaning into Dean’s touch. Dean smiled.

“I’ve got you, Cas,” Dean assured him before rubbing Castiel gently. Castiel lost himself in Dean’s hand and kiss, their heads falling into the pillows.

The three of them moved together, pleasure thrumming through each of their bodies. In what seemed like hours and seconds alike, they were finding their highs, bodies reacting to one another like they’d been doing it for years.

Afterward they laid together, naked again on the bed. Sam was almost dozing when Dean turned to him.

“Does that really do it for you, us wearing your clothes?” Dean asked, genuinely curious.

Sam stretched like a cat, grabbing onto Dean to squeeze affectionately before answering. “Yeah, I guess. I dunno, just seeing you in my stuff…makes you really feel like mine.”

Sam grinned goofily at Dean and Castiel, laid out on his bed. They smiled back.

“We’ll just have to be sure to wear your clothes more often, then,” Castiel said. “They are awfully large and comfortable.”

“Yeah, gigantor, I don’t think it’ll work for you to wear my clothes, but I’ll wear yours if you like it,” Dean offered. Sam chuckled before snuggling back to the pillows.

They fell asleep again, even though it was only late morning. They’d had enough exercise over the past couple days to need all the rest they could get.


	19. Chapter 19

**Notes for the Chapter:**

> This chapter is for the Impala Sex square for SPN Kink Bingo and the Holy Oil square for Heaven & Hell Bingo. Destiel.

Later that afternoon, when they had finally gotten out of bed and moved around, Dean found himself bored. While Sam and Castiel worked in the library, Sam looking for a new case and Castiel translating books that were in Enochian or Ancient Greek, Dean gave Baby a full check-up, did laundry, and cleaned the kitchen.

Cleaning the kitchen is what gave Dean an itch.

“I gotta get out for a bit,” he announced to the others. “I’m going on a beer run, ‘cause we’re all out.”

Sam looked up and nodded. “You could get actual groceries while you’re out, too, ya know,” he suggested. Dean rolled his eyes.

Castiel stood. “I’ll join you.” He looked to Sam. “Perhaps I will be able to convince Dean to get more substantial food than beer.”

Sam grinned as Dean and Castiel headed down the hall, climbing into the fresh and clean Baby.

Dean rolled the windows down and blasted the music, feeling incredibly free and happy. Castiel sat as usual in the passenger seat, enjoying Dean’s happiness as if it were his own.

They shopped around town (Castiel convincing Dean to get more than just beer, although he got quite a bit of beer as well) before pointing the car back toward home. By this point, Castiel was sitting closer to Dean on the bucket seat and Dean’s hand was resting on Castiel’s thigh.

As they left the town limits, Castiel had a rush of interest. His hand met Dean’s and slid it up so that Dean was cupping his crotch, where his erection twitched with interest.

Dean glanced over at Castiel, a glint in his eye. He took his hand away and turned Baby off the road at the next open area of trees, parking her in a secluded alcove.

As he switched the car off, he turned toward Castiel with a raised eyebrow. “Did you want something, Cas?”

Castiel answered by leaning in and taking Dean’s mouth for himself, kissing him with enthusiasm. Dean answered in kind, their tongues battling for dominance. 

Just as Castiel’s hand moved to snake its way up Dean’s shirt, Dean pulled back.

He held a finger up to stop Castiel’s complaint. “I have an idea. Get in the backseat.”

Dean opened his door and went around to the trunk, giving Castiel a moment to process Dean’s order before doing as he said. Castiel was sitting in the open door of the car when Dean came around, placing something on the roof of the car.

“What’s-?” Castiel started, but Dean leaned into the car to kiss him. Castiel laid back, feeling Dean undoing his pants. Castiel slipped out of his jackets while Dean pulled his pants and underwear down, placing a teasing, chaste kiss on the tip of his cock before standing up. 

Dean glanced around, seeing only trees, before undoing his own pants, pushing pants and boxers down in one swift movement. His cock bobbed a hello toward Castiel while Dean slipped his shirts off, and then he was standing in front of Castiel, gloriously naked.

“Dean…” Castiel invited, and Dean grabbed something off the roof of the car before diving into the back with Castiel. They kissed as they tugged the rest of Castiel’s clothes off, his trench coat serving as a blanket between them and the leather seat.

A delicious rut of their cocks against one another started, making Castiel groan. While they found a rhythm, Dean’s hands started to fumble with something. Castiel would have asked, if his mouth wasn’t otherwise occupied. All of a sudden, Dean reached between them and the rut of their bodies was slicked up by something wet.

Castiel pushed Dean back, looking down between them. Dean’s hand was shining with something, which he was using to lube up both of their cocks. “Dean,” Castiel asked, shocked at how breathy his voice was, “what is that?”

Dean grinned sheepishly and glanced down into the floorboards of the backseat. Castiel followed his gaze and his eyes widened as he blushed.

The bottle in which they kept Holy Oil was laying on the floor, cap undone. Castiel was hot all over, thinking of using such a precious liquid for such a raunchy purpose.

“Dean!” Castiel squealed, but he was distracted again as Dean took them both in hand and stroked. Castiel’s head fell back onto the seat, thrusting up against Dean to find even more pleasure.

It didn’t take long, knowing how _wrong_ the Holy Oil should have been, for Castiel to come all over their stomachs and Dean’s hand, and the additional wetness only added more slickness to help Dean come to his own peak. When they’d both caught their breath, Castiel pushed Dean to the side, watching as he fell into the floorboard of the car.

“Ow!” Dean complained, looking at Castiel with betrayal. “Rude!”

Castiel sighed. “Holy Oil is not something to be used for such a-a-“ Castiel searched for the right word. “A _sacrilege_ purpose!”

Dean laughed, awkwardly climbing out of the car and reaching for his clothes. “You weren’t complaining when you came all over us,” Dean pointed out, using his t-shirt to clean himself up before throwing it at Castiel to do the same. Castiel rolled his eyes.

“Well,” Castiel replied. Dean expected to hear more, but it seemed that Castiel had no other arguments.

Dean re-dressed and got back in the driver’s seat, quite happy with the outcome of his beer run.


	20. Chapter 20

**Notes for the Chapter:**

> This is for the Beard Kink square for SPN Kink Bingo and the Dry Humping square for Sam Winchester Bingo. Sastiel!

Castiel helped Dean bring in groceries before disappearing back to the library with Sam. Dean decided to use some of the things they’d bought to make a decent dinner, so he turned on his music in the kitchen and got to work.

Castiel found himself back in front of an Ancient Greek spellbook, trying his best to translate the ingredients and instructions as accurately as possible. He knew how terribly things could go if he miswrote a single word.

Sam sat across from him, searching news sites on his laptop and taking notes now and then. Castiel knew he hadn’t found a new case yet, seeing as Sam hadn’t said a single, “So get this,” since Castiel returned, but Sam would keep working until he did.

Sam’s hair was falling into his face, so much so that Castiel wanted to reach forward to tuck the locks back behind Sam’s ear. In fact, Castiel would love to just comb his fingers through Sam’s hair, feel how soft it was. Sam had showered earlier, and Castiel wondered if Sam had conditioned his hair to make it baby-soft as usual.

Castiel looked back down at his books, realizing he’d been staring at Sam for the past ten minutes instead of working.

Thoughts of Sam had him looking at the hunter once more, and Castiel took note that Sam wasn’t wearing his normal layers of plaid today. Since they’d been so lazy, in bed most of the day, Sam only had on a black t-shirt, one whose sleeves ended right at the swell of Sam’s muscles.

Castiel licked his lips.

He was surprised at the refraction period of his body, wondering fleetingly if his being an angel made his comeback period quicker than a normal human. His heartbeat sped up as he watched Sam swallow, his Adam’s apple mesmerizing.

It was then that Castiel realized that Sam hadn’t shaved since they’d been back. Looking at the longer-than-normal hair on Sam’s chin and jawline, Castiel would guess that he hadn’t shaved since before the case with the witch, which would have been four or five days ago.

Now, instead of his fingers itching to comb through Sam’s long locks, Castiel’s fingers wanted to bury themselves in the hair of Sam’s beard, feeling the wiry bristles between his fingers.

Castiel stood suddenly, knowing that his mind wouldn’t still until he’d done something. Sam looked up at the sudden movement, his mesmerizing eyes watching Castiel’s every move as he rounded the table.

“Do you need something?” Sam asked, confusion forming on his face as Castiel came up right next to Sam.

Castiel didn’t answer, but reached out to Sam’s face and scratched at Sam’s beard. Sam tilted his face slightly to give Castiel a little more access to dig his nails in.

“Mmm,” Sam hummed. “That feels good. It’s at the kinda-itchy stage.”

Castiel smiled, glad that Sam was enjoying himself. But Castiel wanted more.

He grabbed the back of Sam’s chair and moved Sam back from the table, giving Castiel just enough room to straddle Sam’s lap. Sam’s hands automatically found Castiel’s hips, and he looked like he was going to ask another question before Castiel began scratching at Sam’s beard again, with both hands this time.

Sam’s eyes closed and his fingers pressed into Castiel’s hips, giving Castiel every last motivation to lean forward and kiss Sam.

Sam didn’t hesitate to respond with enthusiasm, letting Castiel tilt his head to deepen the kiss. Castiel didn’t take his hands from Sam’s furry face, loving the scratching feeling against his fingers and lips.

Castiel had already been worked up, just from watching Sam for the past however-long, so in no time he was hard as a rock. With the way he was stradding Sam, though, his pants were much too tight to be comfortable. He shifted, trying to ease the pressure, but doing so only caused Sam to hold his hips tighter.

Castiel pulled back from the kiss for just enough time for Sam to moan deliciously, his hips raising to grind against Castiel.

It was then that Castiel felt exactly how excited Sam was, so he dove back into the kiss. Sam took charge, his hands guiding Castiel’s hips in a slow and dirty grind. As Castiel’s hands petted and scratched at Sam’s beard, their lower halves pressed and pulled and rubbed together. Castiel was beginning to sweat, but he couldn’t be bothered to get off of Sam to undress. He didn’t want to stop touching the man, he only wanted more.

Sam’s fingers were surely going to leave bruises on Castiel’s hips, with how tightly and forcefully he was holding Castiel, but neither of them cared. At this point, they were only focused on the grind against each other, chasing their climaxes.

In little time, Sam bit down on Castiel’s lip as he whispered Castiel’s name, his hips jerking in orgasm. Castiel continued to ride him until he orgasmed as well, rubbing his face against Sam’s hairy cheek. They stayed still a moment, cheek to cheek, before Sam moved his hands from Castiel’s waist to wrap around Castiel’s body in a hug.

“Did you get a bit distracted?” Sam asked in a teasing voice. Castiel smiled.

“I suppose. Thanks for getting distracted with me,” Castiel replied. He leaned out of the hug to kiss Sam once more before standing, his legs slightly stiff from the awkward position for so long. “I’m going to go clean up.”

Sam nodded, picking at his damp pants with his fingertips. “I’ll join you.”

Dinner was ready just as they finished changing clothes. Dean gave them a teasingly suspicious glance, but seemed to be happy that Sam and Castiel had gotten some alone time.

Castiel was exhausted, though, as were the brothers. A quick conversation at dinner had them deciding that maybe it would be a good time to take a break from so much sex to concentrate on other aspects of their relationship.

Luckily, Sam found a new case right after dinner and they knew the distraction would keep them busy.


	21. Chapter 21

**Notes for the Chapter:**

> This chapter is for the Panty Kink square of SPN Kink Bingo, the Grace Kink square of Heaven and Hell Bingo, and the Praise Kink square of Dean and Cas Bingo.

The case Sam found was a pretty easy haunting, but Castiel tagged along for fun anyway. The three of them found a crappy motel and even dirtier bar in the town they headed to, but those things couldn’t keep the smiles from their faces. 

Every moment they spent together had them happy, happier than they’d been in a long time. Sure, Dean and Sam had been happy together, but the addition of Castiel to their relationship amplified that tenfold. Things just felt right.

It was when Sam went to return their research material to the library a few days later, after the case was over, that the weight of arousal began settling over them. Dean and Castiel were waiting in the motel room, packing all of their things so that they could head back to the bunker when Sam returned. 

Castiel watched as Dean reached for his duffel bag, his shirt riding up. That’s when he saw it…

A flash of bright blue.

Attention grabbed, Castiel crossed the room to press against Dean as he stood back up. Dean chuckled. “Well hey there, angel,” Dean said, his voice rumbling low. Castiel’s arms wrapped around Dean’s waist in a possessive gesture. “Can I help you with something?”

Castiel spread his fingers against Dean’s abdomen, feeling Dean’s heat through his layers. “Perhaps,” Castiel answered vaguely as his hand moved down to the top of Dean’s jeans. He tucked his fingertips inside, feeling the exact moment that Dean tensed slightly when Castiel’s fingers found soft fabric.

“What is it that you have on under these jeans, Dean?” Castiel asked. He felt Dean’s heartbeat pounding hard, caught like a deer in the headlights.

“Uh…” Dean started, obviously trying to find words. “I hadn’t really been expecting…um…”

Castiel smiled against Dean’s shoulder before turning the hunter around in his arms. He caught Dean’s eye and gave an encouraging smile. “Will you show me?”

Dean fought an internal battle for a moment before taking a deep breath and nodding. “Yeah, Cas,” he said. He stepped backward, out of Castiel’s arms, and undid his jeans. He paused before letting them go, so Castiel gave him an encouraging nod.

Dean let his pants fall to the ground and allowed Castiel to take in the sight… Dean was wearing a pair of bright blue panties, the color of a clear summer’s day and a fabric soft like silk. Castiel reached out to touch the growing line of Dean’s penis but stopped his hand before it got too far.

“May I?” Castiel asked, looking up at Dean’s face. He was worrying his bottom lip between his teeth, looking very self-conscious. He nodded, though, so Castiel’s hand reached farther forward. Castiel’s hand splayed open along Dean’s hip, his thumb and pointer finger feeling the soft fabric and the rest of his hand landing on skin. Castiel could tell Dean was nervous, so he decided to do what he could to let Dean know how much he enjoyed Dean’s panties.

“These look gorgeous on you, Dean,” Castiel praised, lowering himself to his knees in front of Dean. “Such a pretty pair of panties, covering such a pretty cock.”

Dean hummed as Castiel leaned his face toward Dean’s crotch, rubbing his face against the soft fabric that was pulled taught over Dean’s growing erection. Castiel closed his eyes at the feel of the soft fabric, feeling the way it slid smoothly across his cheek. His hands grasped tighter onto Dean’s hips, feeling the small tremors of pleasure and restraint as Dean let Castiel do what he wanted.

Castiel looked up at Dean’s face and smiled. “You look so good in these panties, Dean,” Castiel affirmed again, “I really hope you have more of them to show me.”

Dean nodded, swallowing deep. “Yeah, at the bunker.”

Castiel held Dean’s eye as he placed an open mouth kiss on the stretched fabric that covered Dean’s cockhead. It twitched under the layer and Dean bit his lip to muffle a groan.

Then Castiel got an idea.

He continued kissing and nipping at Dean’s erection through the panties while letting his mind concentrate on something else, gathering a bit of his angelic power to use. His hands held Dean still while he trailed his grace up Dean’s thighs.

“So good, Dean,” Castiel mumbled when Dean tensed up, sensing the extra touches on his body. “So beautiful, so good for me. Just relax…”

Dean did as he was told as Castiel’s grace warmed his skin. It reminded him of the feeling that he’d get when Castiel would heal him after an injury – like a ray of sunlight dancing on his skin, making the surface prickle with comfort. The warmth traveled up his thighs and around to his ass, staying there and squeezing a bit.

Castiel was still nuzzling the packaged cock in front of him as his grace attended to Dean’s cheeks. It dipped into Dean’s crack, nudging his hole, before leaving again, not intruding but just barely teasing.

“Cas –“ Dean gasped, wanting more. Castiel smiled. 

“Pretty panties on a beautiful man,” Castiel mumbled. “Do you want to come for me, Dean?”

Dean nodded. “Yesss….”

Castiel enveloped Dean’s cockhead in his mouth through the panties, tonguing the slit. At the same time, he dipped his grace to nudge at Dean’s hole a little more insistently, until a bit of the warmth fell inside. The pressure inside of him, along with Castiel’s verbal and physical praise on his cock had him creaming his panties, the taste seeping through the thin fabric.

“Very good, Dean,” Castiel said, using his hands to move the ruined fabric out of the way. He cleaned Dean’s cock with his tongue before helping Dean sit back onto the bed, his legs shaking after the surprise interaction. Dean grinned lazily.

“You can get me some clean boxers to change into, my legs are jelly,” Dean suggested. Castiel leaned in for a kiss on the lips before doing as Dean said, helping the hunter gain his balance before Sam returned.


	22. Chapter 22

**Notes for the Chapter:**

> This chapter fills the Blowjobs square for SPN Kink Bingo, the Wing Kink square for Dean and Sam Bingo, The Wing Kink square for Heaven & Hell Bingo, the Cuddle Party square for SPN Poly Bingo, and the Cuddling square for SPN Genre Bingo.

Soon enough the boys were back home in the bunker and Dean was bristling. He had wanted to tell Sam about Castiel’s trick with his grace, but couldn’t find the right words when they were in the car. Just blurting out something like, “Hey Sam, you really need to feel how Cas can use his grace to make you come,” didn’t quite seem right.

They went through the motions of unpacking before meeting in the kitchen for dinner. Sam sat at the kitchen table with his laptop while Dean taught Castiel how to make enchiladas. Dean had showed Castiel how to make food before, but this was the first time that Dean stood behind Castiel, arms wrapped around him to show him just how to chop the ingredients, how to roll the tortillas…all the while placing gentle kisses on Castiel’s neck.

It felt so natural that Dean had to marvel at the situation a few times.

Then they ate, and Dean’s memories of Castiel’s grace on his skin came back to him. He shifted uncomfortably in his chair as he avoided eye contact with the others (who were talking about something or other that Dean zoned out from a few minutes before) to make sure they didn’t notice that he’d popped a random boner in the middle of dinner.

Dean’s shifting caught Sam’s attention, though.

“Dean, what’s your problem?” Sam asked teasingly, not expecting the kind of response he was about to get. Dean couldn’t hold it in anymore.

“Castiel did this awesome thing earlier with his grace to make me come, Sam, you have got to let him do it to you. It was awesome.”

Sam and Castiel looked at Dean, surprised at his outburst, before Sam turned to Castiel. “Your grace?” he asked, wanting more information. Dean rolled his eyes, but was relieved to have finally told Sam about Castiel’s grace. 

Castiel nodded, glancing at Dean. “Yes, it seems that I can use my grace to stimulate in a similar way to how I can use my hands. Dean seemed to enjoy it very much.”

Dean scoffed, eating his last bite of enchilada. “Yes, very much, Cas.”

Sam ignored Dean’s commentary. “What about your wings?” He sat back in his chair, putting his napkin on the table. He was obviously ready to abandon the rest of his dinner for this conversation. “If your grace can manifest somewhat, what can you do with your wings? I’ve always wondered, but never found the right way to ask you about them. I would love to see them, if I can…”

Castiel was quiet for a moment, obviously thinking. Dean waited patiently for his answer; he, like Sam, had always been curious about Castiel’s wings. He thought that he’d maybe seen them all those years ago, when Castiel had saved him from hell, but he couldn’t be sure.

“I believe I can show you my wings, yes,” Castiel finally said. “They are sensitive, though. Shall we move to the bedroom?”

Sam nodded, standing up and moving to the door. Castiel and Dean followed, Castiel taking the lead to Sam’s bedroom. It seemed with some unspoken agreement that Sam’s room was the place for all of them to gather for things like this, so that’s where they ended up.

Castiel stood awkwardly in the middle of the room for a minute, his eyes closed. Dean and Sam watched him, wondering what he was doing. Eventually Castiel opened his eyes.

“I should probably remove my shirt and jacket, so that they may manifest without barriers.” Dean looked over to Sam and shared an unspoken conversation.

In tandem, the brothers advanced on Castiel, Dean capturing Castiel’s mouth in a kiss while Sam found Castiel’s neck, both of them moving to unbutton and unzip Castiel to help him from his clothes.

Castiel gasped in surprise, but it quickly turned to a moan as he became the center of attention, the brothers focusing every effort on him. Soon Castiel was standing in the middle of the room nude, Dean’s hand unable to stay away from the angel’s cock as it became semi-hard.

“Dean…Sam…” Castiel gasped, putting his hands up to push at their shoulders a bit. They backed off immediately, not wanting to overstep. “My wings, let me…”

Sam nodded, moving to sit on the end of his bed and pulling Dean down with him. Castiel stood before them, in all his naked glory, and closed his eyes again. He brought his hands together to clasp them in front of his stomach and the brothers felt something in the room shift.

Their eyes widened as a pair of black wings unfurled from behind Castiel, spreading as much as they could in the small room. Castiel breathed out a long sigh before opening his eyes.

No one spoke, but Sam stood to move closer to Castiel. He reached a hand out before pulling it back, unsure. “May I?” he asked Castiel, who nodded.

Sam reached out again, this time letting his fingertips skim along the feathers. Castiel shivered, drawing Sam’s attention. “Does that hurt? You said they are sensitive…”

Castiel shook his head. “Not _that_ kind of sensitive, unless you injure it like you would an arm.”

Dean found himself smiling as he joined Sam. “You mean…” He raised his hand to caress a section of Castiel’s wing softly, earning a shiver in response. Dean looked down to see Castiel’s cock twitching as well. Dean continued, his voice a little lower, “this turns you on?”

Castiel swallowed deeply before nodding. Sam and Dean shared a look before Sam went back to caressing Castiel’s wing and Dean leaned in for a kiss. Castiel sighed into the kiss, his body overwhelmed with the attention. Sam moved around Castiel so that he could press against the angel’s back, his hands finding purchase on both wings to tease. Dean focused on the human parts of Castiel: his mouth, his nipples, his cock. Castiel was fully hard now, and Dean took him in hand to pump slowly and gently, only wanting to tease for now.

Castiel fell into their touch, letting himself enjoy the attention. They moved together for a few minutes before Sam reached around Castiel’s body to Dean. “Switch,” he suggested, so the brothers exchanged places. 

Dean now focused on Castiel’s feathers, getting lost in their softness as he teased. Sam gave Castiel a deep and passionate kiss before dropping to his knees, swallowing Castiel’s cock in one go. Castiel felt the head of his cock slide easily down Sam’s throat, the tightness of Sam swallowing around him making him cry out. He leaned back into Dean, who wrapped one arm around Castiel’s middle to hold the angel up. He kept working light touches along Castiel’s wing, but now was just as focused on his brother sucking the angel’s cock.

With Dean teasing his wings and Sam sucking his cock, Castiel came in no time. He cried out both of their names, and Dean felt Castiel’s feathers flexing under his fingertips as the angel released into Sam’s waiting mouth.

Castiel collapsed into Dean’s arms, obviously exhausted from the stimulation. Sam stood, helping guide the angel to the bed.

Careful of Castiel’s wings, the brothers laid him down, stripped off most of their own clothes, and laid down on either side of Castiel, keeping him close. Sam and Dean shared a silent _That was awesome _look across Castiel’s chest before pulling the covers up and over them all.

Neither Dean nor Sam were particularly tired, but they were more than happy to lay in bed for a while, cuddled with an angel and his soft wings. Castiel pulled them both close, his wings serving as soft pillows for their heads.


	23. Chapter 23

**Notes for the Chapter:**

> This chapter is for the Sub!Cas square of SPN Kink Bingo and the BDSM square of DeanandCas Bingo. Dom!Dean/Sub!Cas, edging. The BDSM is pretty tame.

The following days in the bunker were relaxed. The boys didn’t have sex, but they spent quality time together doing other things: Castiel helped Dean change Baby’s oil, even though Dean could have done it in his sleep. Sam taught Castiel how to clean his Taurus, loving to watch Castiel’s fingers carefully working on Sam’s favorite gun. They shared walks through the surrounding woods, Castiel pointing out different trees and animals as they passed, telling the brothers about their evolution through time.

The relationship between the three of them was growing stronger, not just because of their sexual compatibility, but also because they genuinely enjoyed each other.

One afternoon, Sam went on an errands run into town, needing to stock up on herbal supplies as well as groceries and general necessities. Dean and Castiel were sitting idly in the library, silence between them not quite easy.

Dean couldn’t keep his eyes off of the angel, who was flipping pages of a book. Dean watched Castiel’s long fingers turn the pages, the blue eyes drifting across words. Dean licked his lips, wanting to bite the pale skin of Castiel’s neck.

He shifted in his chair, his jeans growing increasingly tight. Castiel noticed the movement and looked up at Dean.

Dean could tell that Castiel read him just as easily as the book in front of him, the corner of his mouth quirking up minutely as Castiel closed his book and pushed it away.

“Dean, can I help you with something?”

The way Castiel’s voice sounded, so eager and compliant, brought something up in Dean that he rarely got to play with. Sam was usually in charge in the bedroom, when it was just him and Dean, so Dean was usually the one taking orders.

With the way Castiel was looking, though, so willing… Dean decided it would be a good time to let his dominant self out to play.

Dean stood, walking around to stand behind Castiel’s chair. He put a hand on Castiel’s shoulder and squeezed gently. “Bedroom?”

He phrased it as a question so that Castiel could opt out if he wanted to, but to Dean’s excitement Castiel nodded, standing and heading down the hallway. Dean watched him go, wishing that Castiel wouldn’t wear that damn trench coat all the time, hiding his perky ass.

Dean followed Castiel, noting that even though it was just the two of them, Castiel led them to Sam’s room. That was to Dean’s approval, though, because he was mentally listing all of the things that were stashed in Sam’s room that they could play with. 

He wasn’t sure if he wanted to get out some of the harder toys, like the sounds or the crops, but they had some other things Dean might want to dig into.

Castiel stopped in the center of the room, turning to Dean and waiting. Dean smiled, stepping close to Castiel until their bodies were almost touching. He lifted a hand to Castiel’s cheek and kissed the angel.

“Care to play?” Dean asked. Once the words were out he wasn’t even sure if Castiel would know what he meant, but there was a twinkle in Castiel’s eye that reassured him. Castiel nodded. “What’s your safeword?”

Castiel smiled, Dean could see a blush rising on his cheeks. “Pizza man.” Dean almost laughed, remembering a day a long time ago, and nodded, stepping back from the angel.

“Clothes off, then get on the bed,” Dean ordered, trying to keep the nerves from his voice. Castiel immediately sprang into action, folding his clothes neatly on Sam’s desk and climbing on the bed. Dean turned to Sam’s drawer of toys, his fingers trailing across the various items before finding something that caught his eye. He grabbed the smooth ring and turned to where Castiel was laying on the bed, watching him with interest.

Dean walked the few paces to sit at Castiel’s side, his free hand cupping Castiel’s growing erection. Carefully he slipped the cock ring into place, making sure it sat in the correct place at the base of Castiel’s cock. To Dean’s pleasure, it fit Castiel nearly as well as it fit Dean, so he wouldn’t have to worry about the fit while they played.

Dean pumped Castiel’s cock a few times until the angel reached out for him in response. Dean stood out of Castiel’s reach, moving to the foot of the bed. Castiel’s legs weren’t spread terribly wide, so Dean grabbed each of his ankles and pulled his legs apart. Castiel bit his lip but didn’t protest, making Dean smile.

Like a lion stalking his prey, Dean crawled up the bed between Castiel’s lets until he was eye level with Castiel’s cock. He licked up the shaft with a flat tongue, from the ring to Castiel’s already-leaking tip. Castiel whimpered quietly, but stayed otherwise silent.

Dean nudged Castiel’s legs open a bit further so that he could slide a finger back to Castiel’s puckered hole. Castiel twitched at the touch, so Dean took a second to reach for the drawer where he found a bottle of lube to coat his fingers. Now he massaged the ring gently before pressing inside, watching Castiel’s face carefully. Castiel closed his eyes, feeling every bit of Dean’s finger filling him up. 

With Castiel’s eyes closed, it was easy for Dean to surprise the angel when he took Castiel’s cock into his mouth, deep throating him easily. Castiel’s head jerked off the pillows and he cried out, but Dean only responded by giving him a harsh look that clearly said _Stay quiet_.

Castiel gripped at the bedsheets on either side of his hips as Dean bobbed his head and worked another finger into Castiel’s hole.

Dean played Castiel like a well-practiced song, listening to every whimper and moan that tried to escape from Castiel’s mouth. His fingers worked inside of Castiel, avoiding the place that Castiel would like the most for now. His tongue explored every inch of Castiel’s erection, returning to the places that garnered the most response.

When Castiel was panting heavily, close if not for the cock ring, Dean pulled away, both mouth and fingers, to sit up. Castiel’s eyes widened at the abandonment, clearly wondering why. “Dean…”

The corner of Dean’s lip quirked upward, just watching as Castiel’s breathing steadied back out. When the angel had calmed, Dean’s hand found Castiel’s knee to begin a teasing trail back up his leg. Castiel’s cock bobbed with interest, and soon enough Dean was working Castiel toward orgasm yet again.

For the second time, though, Dean pulled away just as he started to hear the telltale signs of Castiel’s pleasure. This time Castiel’s eyes squeezed shut, hissing through his teeth.

Dean watched as Castiel calmed yet again before starting the cycle over.

With each round of edging, Castiel grew more and more desperate. His whimpers were frantic, desperate for anything from Dean. When Dean’s finger started to work Castiel’s prostate as well, he thought Castiel might just cry.

During the fifth or sixth time – Dean had lost count – Castiel’s hands finally let go of the bed to grasp at Dean’s head, wanting to keep him from pulling away. Instead of complying, Dean slapped his hand away playfully, standing up. 


	24. Chapter 24

**Notes for the Chapter:**

> This chapter is for the Coirus Interruptus square for SPN Kink Bingo and the Bondage square for Dean and Cas Bingo.

Dean slapped his hand away playfully, standing up. Without much thought, he went to grab Castiel’s blue tie, which he quickly tied around the ring at the top of Sam’s bed and onto Castiel’s wrists.

“Let’s keep your hands up here, okay angel?” Dean cooed, caressing Castiel’s face with his fingertips. Castiel arched into the touch and hummed, his hands flexing slightly to test the restraints.

Dean nodded, satisfied with Castiel’s bindings. They both knew that the angel could get out of the tie easily – too easily, really – but it was the idea of it that made it all amounts of exciting.

Castiel’s cock was red and leaking from the edging, so Dean decided to give him a bit of a break. Dean stood beside the bed, eyes never leaving Castiel’s beautiful form while he removed his own clothes, finally freeing his own neglected erection. He’d been teasing Castiel for so long and ignoring his own needs, which meant that his cock wept at the first touch of his hand.

Castiel could only watch as Dean touched himself, careful and slow to not tease too much.

“Dean, please…” Castiel finally said, the desperation of his voice making Dean squeeze the base of his cock to keep from coming just at the sound of Castiel’s pleas.

“I got you, Cas,” Dean assured him, leaning down to kiss Castiel gently as he climbed on top of the angel. Their cocks bumped against each other, both throbbing with need as they kissed. Once again Dean’s fingers slipped between Castiel’s cheeks to tease his hole, but now he pushed them inside with more of a purpose: he wanted to be inside of Castiel as soon as possible. Castiel’s legs spread helpfully, his hands gripping the tie above his head.

“Dean, need you, please,” Castiel whined again, panting into Dean’s mouth. Dean bit Castiel’s lip gently before pulling away to tuck Castiel’s knees up higher. He teased his cock at the wet opening of Castiel’s hole.

He pushed inside slowly, never breaking eye contact with Castiel. He noticed how Castiel’s hands gripped harder on the tie that bound them, how his breath caught as Dean breached him, how his eyes sparked with arousal. Castiel’s cock was pulsing with interest, the cock ring keeping him in check.

Finally Dean was fully seated inside of the angel and he leaned forward, folding Castiel nearly in half to kiss him hard on the mouth. Dean held still as they kissed, even as Castiel twitched below him. Dean almost missed Castiel’s touch enough to untie the binds around Castiel’s wrists, but there was a thrill of excitement inside as well, knowing that Castiel was giving Dean all the power.

Dean started to move then, not breaking their kiss but just rocking his hips back and forth enough to garner some friction. Castiel’s cock was trapped between them, leaking from the tip and unable to come. Dean moved slowly, teasing them both with the drawn out movements. The kiss was as dirty as the slow, rocking movement of their hips, their breaths mingling between them as the air grew heavy.

They were so wrapped up in each other that they didn’t notice the door to Sam’s room opening, revealing them to the younger Winchester.

While he was a little surprised to find Dean and Castiel in his bed, he was definitely not disappointed. He had a fine view of Dean’s bare ass, thrusting gently into the angel below him. Sam quietly put his things down, going ahead and slipping his shoes off and removing his outer shirt. He then cleared his throat, making Dean freeze and look over his shoulder at the surprise intrusion.

“Mind if I join?”


	25. Chapter 25

**Notes for the Chapter:**

> This chapter fills the Double Penetration square for SPN Kink Bingo, the Double Penetration square for Dean and Cas Bingo, the Poly-Fic square for SPN Genre Bingo, and the Free Space for SPN Poly Bingo.
> 
> I hope you enjoyed reading this fic as much as I enjoyed writing it! Trying to fill all 25 of my kink bingo fills with one cohesive (or as cohesive as a smutfest could be) story was a challenge that I really enjoyed. This actually filled 57 bingo squares total, if my count is correct!

“Mind if I join?”

Dean smiled at his brother over his shoulder before looking back down at Castiel. “Fine with me, Sammy. You mind, Cas?”

Dean ended the question with a deeper thrust into the angel, making Castiel gasp before he could answer. 

“Come on, then,” Castiel replied once he’d gotten his voice back. Sam walked over to the side of the bed, removing clothes until he stood next to them naked. His cock was already in the game, the sight and smell of sex getting him hard in no time.

Sam took note of the tie that bound Castiel’s hands and he smiled, glad that Dean had been a bit creative. When Dean sat up, letting Castiel unfold a bit while still rolling his hips into the angel, Sam also noticed the glint of silver around Castiel’s cock.

“Mmm,” Sam hummed, enjoying the front-row view. “Where do you want me?”

If Dean was surprised that Sam hadn’t taken immediate control of the situation, he hid it well. Dean thrusted a little harder into Castiel twice before answering. “Cas, you wanna suck Sam’s cock?”

Castiel nodded, licking his lips like he was desperate for it. “Come closer, Sam,” Castiel said, his voice sounding wrecked. The deep timbre held more gravel than usual and it made Sam desperate to spill down that throat.

Sam assessed their position, deciding where to put himself. In the end, he just knelt on the pillows next to Castiel’s head. Castiel turned his head and immediately started licking and sucking at Sam’s cock like a man starved.

Sam groaned, one hand finding its place on Castiel’s head to steady himself. He looked over at Dean, whose eyes were now hooded as he watched Castiel’s tongue on Sam’s cock. 

Sam reached for his brother with his free hand, grabbing Dean’s head by the hair and pulling him in for a kiss. They continued to thrust into Castiel beneath them while they made out, getting more desperate for release with every second. 

Eventually Dean had to pull away from Sam to concentrate on his movements. He grabbed at Castiel’s hips and hoisted them just a bit higher, letting his cock drive deeper and harder into Castiel’s prostate with each thrust. Dean was letting out little grunts of desperation now, chasing the orgasm that was too close. With just a few more thrusts he was coming, spilling into Castiel. 

Sam watched as Dean came, Sam’s hand reaching to remove the cock ring from Castiel’s erection. He threw it to the side and pumped Castiel’s cock only three times before spunk was coating Castiel’s chest. Sam’s cock fell from Castiel’s lips as he cried out, so Sam took himself in hand and in no time his seed was mixing with Castiel’s.

Dean, recovered from his orgasm, watched as the final drops mixed before leaning down and lapping the sticky liquid up with his tongue, savoring the flavor of Castiel and Sam mixed together. He reached for them both and pulled their faces in for a messy kiss, sharing the taste between their tongues.

When the kiss broke, all three of them had smiles on their faces. They couldn’t help it; an overwhelming happiness was shared between the three of them whenever they spent time together.

Dean pulled away first, going for a washcloth as Sam unbound Castiel’s wrists and massaged his arms. Dean cleaned them all up before throwing the cloth across the room toward Sam’s laundry bin. Normally Sam might have scolded him, but right now he didn’t bother. Instead he pulled the bedsheets down, letting the three of them climb under. 

Castiel laid between the brothers, completely exhausted from the past hour. He wouldn’t trade a second of it, though, happy as he was with the Winchesters.

Just as he was falling asleep, he mumbled, “Love you.”

Sam and Dean’s eyes met above the sleepy angel. “Me too,” Dean replied softly.

Sam grinned, his eyes sparkling at his brother’s admission. “So much,” Sam agreed.


End file.
